Name: 5418-63-3|1,2,3,3-Tetramethyl-3H-indolium iodide|98%
Brand: Ambeed
SKU: A142082
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1
[ 1640-39-7 ]
[ 74-88-4 ]
[ 5418-63-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	In neat (no solvent) at 120 - 140℃; for 0.333333h; Microwave irradiation; Green chemistry;	4.5. Microwave synthesis of indolenine salts 3-11 General procedure: Individual indolenine derivative, 2,3,3-trimethlyindolenine, 1, or 2 was added to a 10-mL microwave vessel equipped with a micromagnetic stir bar along with appropriate alkyl iodide (1.2 mol eq.). The reaction vessel was securely capped and then subjected to microwave irradiation for 20 min allowing for the complete transformation of the heterocyclic starting material to the corresponding salt. The resulting residue was filtered, dried overnight on vacuum and the corresponding salts were obtained in 98% yield in excellent purity as determined by NMR (1H and 13C)spectroscopy
98%	In acetonitrile for 24h; Reflux;
97%	at 110℃; for 4h;

96%	In nitromethane at 20℃; for 12h;
96%	In 1,2-dichloro-benzene at 110℃; Inert atmosphere;
96%	In acetonitrile for 11h; Inert atmosphere; Reflux;
96%	In nitromethane at 20℃; for 24h;	1.1 2,3,3-Trimethyl-3H-indole (1.59 g, 10 mmol) was dissolved in nitromethane (30 mL). Methyl iodide (2.13 g, 15 mmol) was added thereto. React at room temperature for 24 h, There is a lot of solid precipitation, Ethyl ether was added thereto to completely precipitate it. Then filter under reduced pressure, Rinse with ether, The solid product is 1,2,3,3-tetramethyl-3H-iodoindole, The yield was 96%.
96%	In nitromethane at 20℃; for 24h;	1.1 The specific procedure is as follows: 2,3,3-trimethyl-3H-indole (1.59 g, 10 mmol) is dissolved in nitromethane (30 mL), and then iodomethane (2.13 g, 15 mmol) is added thereto, and reacted at room temperature. 24h, A large amount of solid precipitated, diethyl ether was added thereto to completely precipitate, and then filtered under reduced pressure. rinse with ether, the solid product was 1,2,3,3-tetramethyl-3H-iodoindole in a yield of 96%.
96%	In nitromethane at 20℃; for 24h;	1.1 2,3,3-Trimethyl-3H-indole (1.59 g, 10 mmol) was dissolved in nitromethane (30 mL).Methyl iodide (2.13 g, 15 mmol) was added thereto.After reacting at room temperature for 24 h, a large amount of solid precipitated.Ethyl ether was added thereto to completely precipitate it.Then filtered under reduced pressure and rinsed with ether.The solid product is 1,2,3,3-tetramethyl-3H-iodoindole,The yield was 96%.
96%	In nitromethane at 20℃; for 24h;	1.1 The specific process is: dissolving 2,3,3-trimethyl-3H-indole (1.59 g, 10 mmol) in nitromethane (30 mL),To this was added methyl iodide (2.13 g, 15 mmol),24h reaction at room temperature,A large amount of solid precipitated out, and ether was added to it to completely precipitate.It was then filtered under reduced pressure and rinsed with ether.The solid product was 1,2,3,3-tetramethyl-3H-iodoindole,The yield was 96%.
96%	In toluene for 6h; Reflux;	Experimental Procedure for the Synthesisof 1,2,3,3-tetramethyl-3H-indolium Iodide (2) Compound 1 (0.5 g, 4.399 mmol) was dissolved in toluene(10 mL) and iodomethane (0.85 mL, 13.207 mmol) wasadded at room temperature and the reaction was refluxedfor 6 h. during the reaction the solid precipitate was formed.The reaction mixture was cooled to room temperature andthe solid was filtered and washed with diethyl ether (20 mL).The resulting white crystalline solid was used for next stepwithout purification. Yield: (0.734 g, 96%), mp 258 - 260, 1H NMR (DMSO-d6, 600 MHz) δ 7.94 - 7.92 (m, 1H),7.86 - 7.83 (m, 1H), 7.64 - 7.61 (m, 2H), 3.99 (s, 3H), 2.80(s, 3H), 1.54 (s, 6H); 13C NMR (DMSO-d6, 150 MHz) δ196.4, 142.5, 142.0, 129.7, 129.2, 123.7, 115.6, 54.4, 35.3,22.2. HRMS m/z calculated for C12H16N+(M)+: 174.1277,found: 174.1280.
95%	In toluene at 80℃; for 48h; Inert atmosphere;
95%	In toluene at 80℃; for 48h;
95%	In acetonitrile at 100℃; for 4h; Inert atmosphere;
94%	In acetonitrile at 150℃; for 0.5h; Microwave irradiation;
94%	In acetonitrile Reflux;
94%	In acetonitrile Reflux;
94%	In acetonitrile at 80℃; for 12h;
93%	at 110℃; for 0.0416667h; microwave irradiation;
93%	In acetonitrile for 7h; Reflux;	1. Synthesis of 1,2,3,3-Tetramethyl-3H-indolinium iodide (1) 2,3,3-Trimethylindolenine (1.0 g, 1.01 mL, 6.28 mmol, 1 eq) was dissolved in acetonitrile (5 mL) and then methyl iodide (0.43 mL, 6.91 mmol, 1.1 eq) was added. The reaction mixture was heated at reflux for 7 h, cooled to room temperature and the precipitate was collected by filtration, washed with diethyl ether, and dried in vacuo over potassium hydroxide pellets. Product 1 was obtained as pink crystals with 93 % yield (1.76 g, 5.84 mmol). Mw = 301.17 g/mol (C12H16IN).
92%	In acetonitrile for 2h; Reflux;
91%	at 20℃; for 24h;
91%	In acetonitrile for 0.25h; Microwave irradiation;	2.2.2. Synthesis of 1,2,3,3-tetramethyl-3H-indolium iodide (3) A mixture of 2,3,3-trimethyl-3H-indole (2.0 g, 12.6 mmol) andmethyl iodide (4.71 mL, 75.3 mmol) in acetonitrile (7.8 mL) was heatedat refilux,u sing microwave irradiation for 15 min (130 W) (open vessel).The reaction mixture was cooled to room temperature and the solventevaporated under reduced pressure. The residue obtained was trituratedwith diethyl ether (20 mL) and the solid was recrystallized frommethanol-diethyl ether. The pale yellow crystalline product was filtered,washed with diethyl ether and dried under vacuo over P2O5. Yield 3.42g, 91%. 1H NMR (300 MHz, DMSO-d6) δ: 1.53 (s, 6H), 2.77 (s, 3H), 3.97(s, 3H), 7.64-7.62 (m, 2H), 7.82-7.84 (m, 1H), 7.90-7.92 (m, 1H).
90%	In nitromethane at 20℃; for 12h; Inert atmosphere;
90%	In acetonitrile
90%	With nitromethane at 20℃; for 12h;
90%	In acetonitrile Reflux;
90%	In acetonitrile at 100℃; for 16h; Inert atmosphere;	3 Example 3: General procedure for the synthesis of l-alkyl-2-methyl-3,3-dialkyl-3H- indol-l-ium iodide and 5-carboxy-l-alkyl-2-methyl-3,3-dialkyl-3H-indol-l-ium iodide (5a, 5b, 6a, 6b, 7a and 7b): General procedure: Alkyl iodide (2 equiv.) and corresponding 2-methyl-3,3-dialkyl-3H-indolederivative (1 equiv.) were dissolved in MeCN (60 mL) in a 100 mL round bottom flask and refluxed at 100 °C for 16 h under inert atmosphere. The reaction mixture was cooled to room temperature (27°C); the solvent was removed under reduced pressure. The precipitate was washed with diethyl ether (4x 5 mL) to afford the required compound as a red color liquid in case of 7.
90%	In acetonitrile at 45℃; Reflux;	Synthesis of product E 2,3,3-Trimethylindolenine (5 mmol, 0.80 g) was dissolved in 15 mL of acetonitrile, when heated to45°C with stirring, 3 mL of methyl iodide was added and refluxed overnight. The solution was cooledand filtered to obtain a pink needle-like solid (1.36 g, yield 90%).
90%	In ethanol at 80℃; for 8h; Inert atmosphere;	1.1 1) Synthesis of compound 1 1) Take 2,3,3-trimethyl-3H-indole (159.23mg, 1mol) and methyl iodide (3mol) and dissolve them in 20mL ethanol to obtain a mixture; under the protection of nitrogen, stir, The reaction was carried out under reflux at 80°C for 8 hours. When a solid precipitated, filtered under reduced pressure, washed with ethanol, and dried to obtain a pale pink solid, compound 1, and the reaction equation is as follows:The yield of compound 1 is 90%, without purification, proceed directly to the next step reaction;
89%	In toluene at 80℃; for 48h; Inert atmosphere;	Synthesis of N-methyl-2,3,3-trimethylindolinium iodide 2 This compound was synthesized following a previously published procedure. 1 A solution of 2,3,3-trimethylindolenine (3.0 g, 18.8 mmol) and iodomethane (3.2 g, 22.7 mmol) in toluene (60 mL) was heated at 80 C for 48 h in a 120 mL Ace pressure tube. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue obtained was suspended in hexanes (100 mL), sonicated for 10 min and filtered to obtain product as a brown solid (5 g, 89 %).
86%	In acetonitrile for 12h; Reflux;
86%	at 140℃; for 6h;	1 In the 2, 3, 3-trimethyl -3H-indole (and optical pure medicine industry system ) 63 parts of methyl iodide is added in (and optical pure medicine industry system ) 65 parts, to 140 °C heating reflux for 6 hours. After cooling, adding diethyl ether 120 parts, to obtain the precipitate is filtered, washed with cold acetone after use, drying under reduced pressure to obtain destannylation 1-methyl -2, 3, 3-trimethyl -3H-indolium 102 parts (86%). Then the pyridine 470 parts, triethylamine 64 and destannylation 1-methyl -2, 3, 3-trimethyl -3H-indolium 100 and O-cresol acid ethyl ester (and optical pure medicine industry system ) 64 parts, to 120 °C reaction 1 hour. After cooling, slowly added diethyl ether 800 parts, the filter is created. This solid using ethanol after crystallization again, in order to 60 °C reduced-pressure drying 24 hours, formula (g-1) indicated that compound 145 parts (90%).
85%	In acetonitrile at 85℃; for 24h; Inert atmosphere;	1 Manufacturing example 1 Under N2, 10 g (62.80 mmol, 1 eq) of the compound 1a and 13.37 g(94.20 mmol, 1.5 eq) of 1b was added to 100 ml of acetonitrile, was stirred at 85°C for 24 hours. After cooling to room temperature, the precipitate was filtered off under reduced pressure, washed with CHCl3 and dried,16.068 g (53.35 mmol) of the compound 1c was obtained. Yield 85%
85.3%	In ethanol at 80℃; Sealed tube;
85%	In acetonitrile for 12h; Inert atmosphere; Reflux;	Synthesis of 1 2,3,3-Trimethylindolenine (796.15 mg, 5 mmol) andiodomethane (4258.80 mg, 30 mmol) were dissolved inacetonitrile (40 mL). The solution was stirred under aninert nitrogen atmosphere at reflux for 12 h. On cooling,the resulting solution was filtered and the brown precipitatewas washed with diethyl ether and then driedin vacuum to afford 1 (1280.00 mg, 85%).1H NMR(DMSOd6, 400 MHz) δ 7.90 (d, J = 5.9, 2.9 Hz, 1H), 7.82(t, 1H), 7.64-7.60 (m, 2H), 3.96 (s, 3H), 2.75 (s, 3H), 1.52(s, 6H), (Figure S1).
85.7%	In acetonitrile at 80℃; for 8h;
85.8%	In acetonitrile at 80℃; Inert atmosphere; Schlenk technique;	Synthesis of compound 1 2,3,3-Trimethyl-3H-indole (4.0 mL, 25mmoL) was dissolved in CH3CN (15 mL). To the mixture was added CH3I(4.0 mL, 60 mmoL). Then the mixture was refluxed at 80 °C overnightunder argon atmosphere. After cooling to room temperature, the precipitatewas filtered and washed with n-hexane and dried in vacuum toobtain compound 1 as a pale pink solid powder (6.68 g, yield 85.8%). 1HNMR (400 MHz, DMSO-d6) δ (ppm) 7.92 (dd, J = 8.81 Hz, 1H), 7.84 (m,J = 8.57 Hz, 1H), 7.63 (m, J = 22.25 Hz, 2H), 3.98 (s, 3H), 2.77 (s, 3H),1.53 (s, 6H).
84%	In toluene at 80℃; for 288h;
84%	In toluene at 80℃; for 12h;	A solution of 2,3,3-trimethyl-3H-indole (200 μl_, 1.3 mmol) and MeI (100 μl_, 1.6 mmol) in PhMe (20 imL) was heated at 80°C for 12 h under N2. After cooling down to ambient temperature, the solvent was distilled off under reduced pressure. The residue was suspended in hexane (20 ml_), sonicated for 30 min and filtered off to afford the iodide salt of 6 (84%, 0.33 g) as a purple solid. FABMS: m/z = 174 [M - I]+; 1H-NMR (300 MHz1CDCI3): δ = 1.69 (6H, s), 3.13 (3H, s), 4.30 (3H, s), 7.55-7.58 (2H, m), 7.59-7.62 (2H1 m), 7.66-7.67 (1H, m); 13C-NMR (100 MHz1CD3CN): δ = 14.5, 21.9, 35.3, 54.8, 115.4, 123.7, 129.6, 130.3, 142.1.
84.92%	In acetonitrile at 70℃; for 5h;	2 Synthesis of Compound B: 2,3,3-trimethyl 3H (7.95 g, 50 mmol),Methyl iodide (21.30 g, 150 mmol) and 25 mL acetonitrile were added to 100 mLIn a one-neck round bottom flask, the temperature was raised to 70 ° C for 5 hours.After cooling the reaction solution to room temperature, a large amount of purple-red solid was produced in the system.Filter by suction and rinse the filter cake with ethanol.A yellow solid powder was obtained.The crude product was recrystallized from 250 mL of isopropanol.Obtaining 12.78 g of pale yellow needle crystals,The yield was 84.92%.
84%	at 125℃; for 8h;
82%	In butanone Reflux; Inert atmosphere;
81%	at 60℃; for 1h; Inert atmosphere;
81.3%	With nitromethane at 20℃; for 24h;	1.1 (1) In a 250mL round bottom flask, 2,3,3-Trimethylindole 1eq (8.02mL, 0.05mol) and CH3I5eq (15.56mL, 0.25mol) were dissolved in 100mL of nitromethane, and the reaction mixture was reacted at room temperature for 24h, After spin-drying the solvent, a white compound is obtained, Use a dichloromethane/methanol system with a volume ratio of 10:1 to separate and purify the product through a column. To obtain the intermediate compound 1a, The yield was 81.3%;
80%	at 120℃; for 0.0833333h;	1 roiBOi) nd iodoiBetnane (0.44 rniL 7, nan) wer a.dded to a small ffliemwave vial and heated to 120 *C fr 5 miji. The fflixture wis cooled, filiered, arid ash ke-iIled:etero -gm-.Q g (80%) pale piak powiety solid. Spectra data matched those previously reported? B R (400 Ml D S0) -S 7.98 - 7.87 (m. 1 Bp 7.85 7.7 inp IO): 7.67- 7.57 (fp, 2 397 (s; 3H), 2.77
80%	In acetonitrile at 80℃; for 24h;	1-1 Example 1-1: Synthesis of Intermediate 1 compound 100 ml of acetonitrile was added to 2,3,3-trimethylindolenine (0.12 mol) and iodomethane (0.38 mol), followed by stirring at 80° C. for 24 hours.The resulting precipitate was filtered, washed with acetone, and dried to obtain a mixture containing the intermediate 1 compound in a yield of 80% as a white solid.
78.6%	In acetonitrile for 72h; Reflux;	1 Intermediate 3: 1,2,3,3- Tetramethyl- 3H- indole- 1- iodonium 2,3,3-Trimethyl-3H-indole (3.3 g, 21.0 mmol)Methyl iodide (4g, 12.3 mmol)Dissolve in 20mL acetonitrile in refluxing reaction for 72h. After the reaction is completed, cool down. Precipitate, precipitate, filter. Rinse the precipitated solid several times with cold ethyl acetate and place in a vacuum oven to obtain a white solid powder 1 (3.1g). The yield was 78.6%. The product is of high purity and can be used directly in the next reaction without further purification.
76%	In chloroform	4 Synthesis of 1,2,3,3-tetramethylindolenium iodide EXAMPLE 4 Synthesis of 1,2,3,3-tetramethylindolenium iodide 2,3,3-Trimethylindolenine (1.7 g, 10.5 mmols) and methyl iodide (1.5 g, 10.5 mmols) were dissolved in 5 ml of chloroform and heated in a sealed tube at 80° C. for 46 hours. The resulting red precipitate was filtered and washed in turn with iced chloroform and ether to give 1,2,3,3-tetramethylindolenium iodide (2.4 g, 8.0 mmols) as a pale red powder (yield 76%).
75%	In chloroform at 80℃; for 21h;
75%	at 20℃; for 24h;
72.4%	In acetonitrile at 80℃; for 6h;
70%	at 50℃; for 2h;
67%	at 120℃; for 0.333333h; Sealed tube; Microwave irradiation;
60%	In acetonitrile at 80℃; for 2h;	1.2 Step2: Dissolve indole (2.871g, 0.018mol) and methyl iodide (7.69g, 0.054mol) in 20mL of acetonitrile, and stir at 80 for 2h. After cooling to room temperature, it was filtered and washed with cold ether. get1,2,3,3-tetramethyl-3H-indole-1-iodineCompound, yield 60%.
58%	for 24h; Reflux;	1 4.1.1 1,2,3,3-Tetramethyl-3H-indol-1-ium iodide (1a) (0014) 2,3,3-Trimethylindolenine (63.0mmol) was dissolved in iodomethane (168mmol) and with constant stirring, the solution was refluxed for 24h. The precipitate produced was filtered under suction, washed with n-hexane and dried in vacuo to yield the product (58%) as a pink solid. (0015) 1H NMR (d6-DMSO, 300MHz): δ 7.90 (t, J=6.0Hz, 1H, Ar-H), 7.82 (t, J=6.0Hz, 1H, Ar-H), 7.66-7.61 (m, 2H, Ar-H), 3.96 (s, 3H, N-CH3), 2.75 (s, 3H, C-CH3), 1.52 (s, 6H, C-(CH3)2). 13C NMR (d6-DMSO, 75.4MHz): δ 196.45, 142.56, 142.05, 129.77, 129.28, 123.76, 115.57, 100.00, 54.38, 22.14, 14.51. IR (ATR, cm-1): 2968.4, 1628.9, 1455.1, 1392.7, 1357.8, 774.4. MS (ESI) m/z: 174.09 [M+]. Melting point=255-257°C.
58%	at 200℃; for 17h;	7 Example 7 - Preparation of 2,3,3-trimethyl-1 -(methyl)-indolium inner salt (For Cvanine Dye No. 7) 2,3,3-Trimethylindolenine (1 .00g, 0.0063mols) was dissolved in methyl iodide (10.5 mL, 0.1685mols) and with constant stirring, the solution was refluxed at 200°C for 17 hours. The precipitate produced was filtered under suction, washed with hexane and dried in vacuo to give 1 .05g (58%) as a pink solid: 1 H NMR (DMSO, 250 ΜΗζ)δ 7.91 (t, 1 H, Ar-H), 7.82(t,1 H, Ar-H), 7.64(m, 2H, Ar-H), 3.92(s, 3H, N-CH3), 2.75(s, 3H, C-CH3), 1 .51 (s, 6H, C-(CH3)2.13C NMR (DMSO, 250MHz) δ ppm 15.1 , 22,2, 38.4, 57.2, 1 18.3, 121 .9, 122.3, 122.9, 142.1 , 142.3, 195.2.IR (ATR) 2965, 1630, 1481 , 938, 776 cm"1. MS-EI: 174 [M-l ]. Melting point = 257 - 260 °C.
56%	for 24h; Reflux;
45%	In acetonitrile for 24h; Inert atmosphere; Reflux;
37%	In acetonitrile at 80℃; for 7h;	1,2,3,3-Tetramethyl Indolenium Idodide (3a). 2,3,3-Trimethylindolenine (1 g, 12.56 mmol), acetonitrile (50 mL),and methyl idodide (0.94 mL, 15.072 mmol) were refluxed at 80 °C for 7 h. The resulting pink precipitate was filtered and washed with ice-cooled chloroform. Yield: 37%. 1HNMR (500 MHz, DMSO) δ 1.5 (s, 2x3H), 2.7 (3H, s), 3.9 (s,3H, s, N-CH3'-H) 7.6-7.9 (3x1H, m, Ar'-H).
	In chloroform Heating;
	Heating;
	In chloroform	15 EXAMPLE 15 EXAMPLE 15 To a solution of 16.0 g of 2,3,3-trimethylindolenine in 100 ml of chloroform was added 15.9 g of methyl iodide, and the mixture was heated at 80° C. for 21 hours in an autoclave. The resulting precipitate was separated off by filtration to obtain 27.5 g of 1,2,3,3-tetramethylindolenium iodide in the form of white crystals.
	In chloroform	6 Example 6 Example 6 To a solution of 16.0 g of 2,3,3-trimethylindolenine in 100 ml of chloroform was added 15.9 g of methyl iodide and the mixture was heated in an autoclave at 80°C for 21 hours. The resulting precipitate was collected by filtration to give 27.5 g of 1,2,3,3-tetramethylindolenium iodide as white crystals.
	In toluene at 20℃; for 58h;
	In acetonitrile for 3h; Inert atmosphere; Reflux;
	In toluene Reflux;
	In acetonitrile for 3h; Reflux; Inert atmosphere;
	In 1,2-dichloro-ethane at 20℃; for 5h; Reflux;	1 Preparation of compound 2: A solution of 2,3,3-trimethyl-3H-indole and iodomethane in dichloroethane is refluxed by stirring for 4 h. Then the reaction mixture is stirred for one hour at room temperature and the precipitated solid is collected by filtration.
	In acetonitrile Reflux;
	In acetonitrile for 24h; Reflux;
	In acetonitrile for 12h; Reflux;
	Reflux;
	In dichloromethane for 4h; Reflux;	1 Preparation of Compound 2: Preparation of Compound 2: [0109] A solution of 2,3,3-trimethyl-3H-indole and iodomethane in dichloroethane is refluxed by stirring for 4 h. Then the reaction mixture is stirred for one hour at room temperature and the precipitated solid is collected by filtration.
	In dichloromethane Reflux;
	In chloroform at 20℃;
	In acetonitrile Reflux; Inert atmosphere;
	Reflux;	Scheme 1 outlines the synthesis of a series of 700 nm NIR emitting pentamethine cyanine dye derivatives 10-15. The key step is the quaternization of the nitrogen atom in indolenine derivatives 1-3 in either refluxing acetonitrile or toluene for between 10 hours and 3 days, depending on the alkylating agent, to yield the cationic salts 4-9. Condensation of salts 4-9, in a two molar ratio, containing an activated methyl group with malonoaldehydebisphenylamine hydrochloride under basic conditions, normally achieved through the addition of triethyl amine or sodium acetate, furnished the pentacyanines in 70 to 90% yield, as depicted in Scheme 1, in less than 6 hours.
	In acetonitrile Reflux;
	In acetonitrile Reflux;
	at 80℃; for 24h;
	In acetonitrile at 90℃;
	In acetonitrile Reflux;
	In neat (no solvent) at 120 - 140℃; for 0.333333h; Microwave irradiation; Inert atmosphere; Green chemistry;	4.5 Microwave synthesis of indolenine salts 3-11 General procedure: Individual indolenine derivative, 2,3,3-trimethlyindolenine, 1, or 2 was added to a 10-mL microwave vessel equipped with a micro magnetic stir bar along with appropriate alkyl iodide (1.2moleq.). The reaction vessel was securely capped and then subjected to microwave irradiation for 20min allowing for the complete transformation of the heterocyclic starting material to the corresponding salt. The resulting residue was filtered, dried overnight on vacuum and the corresponding salts were obtained in 98%+yield in excellent purity as determined by NMR (1H and 13C) spectroscopy.
	In toluene at 92℃;
	In acetonitrile
16.1 g	In acetonitrile for 10h; Reflux;	1 A round-bottomed flask of 300mL containing the stirrer,9.7 g of 2,3,3-trimethylindolenineAnd 25.9 g of 1-iodomethane,And 85 mL of acetonitrile were added,And the mixture was stirred for 10 hours while heating under reflux.After cooling to room temperature,The reaction solution was added to 425 mL of diisopropyl ether,After cooling on ice,It was left to stand for 30 minutes.after that,The precipitate was collected by suction filtration,The obtained solid was dried under reduced pressure to obtain 16.1 g of a pale pink solid.
	In methanol
	In acetonitrile at 100℃;	General procedure: In parallel, substituted hydrazines 1 (4.0 g, 22.25 mmol) were reacted with 3-methylbutanone(3 mL, 28.04 mmol) in acetic acid and heated to a 100 °C for 24 h. The solution was then neutralizedusing sodium bicarbonate and extracted using dichloromethane; affording substituted indolenineheterocycles 2 which was dried under reduced pressure. The heterocycles 2 were then reacted withan alkyl halide in acetonitrile at 100 °C for 12-18 h. The quaternary ammonium salts 3 were precipitatedwith diethyl ether, and collected.
	In acetonitrile for 8h; Reflux;	1.a a) Synthesis of 1,2,3,3-tetramethyl-3H-indol-1-ium iodide (6): 2,3,3-trimethyl indolinine (3 g, 18.8 mmol), 6 methyl iodide (5.35 g, 37.7 mmol) and 80 mL of 7 acetonitrile were heated 110° C. for 8 h. After this period the remaining solution was cooled. It was concentrated with reduced pressure and then it was washed with diethyl ether (3×30 mL). The yield of 8 compound was show shining pink color solid. It was characterized by 1H-NMR by using CDCl3 solvent it was given below (δ, ppm., J(Hz)): J=1.67 (6H, s, (CH3)2); J=4.31(3H, s, (CH3); J=3.11 (3H, s, N-CH3); J=7.57-7.67 (4H, m).
	In acetonitrile for 6h; Reflux;	2.1 (1) Intermediate 8 Synthesis of ((1Ε,2Ε)-4-((E)-1,3,3 Trimethylporphyrin-2-methylene)-N-phenyl-2-propenyl-1-imine) Compound 6 (2,3,3-trimethyl-3H-indole) (1.6 g, 10 mmol) and methyl iodide (2.8 g, 20 mmol) were dissolved.In 20 mL of anhydrous acetonitrile, the reaction was stirred under reflux for 6 h; after completion of the reaction, it was cooled, and the precipitated pink solid was filtered, washed and dried to give compound (7 1,2,3,3-tetramethyl-3H-indolium iodide); Compound 7 (1,2,3,3-tetramethyl-3H-indolium iodide) (2.1 g, 7 mmol) and the condensing agent malondialdehyde diphenylamine hydrochloride (2.6 g, 10 mmol) were dissolved in 30 mL positive In a butanol-toluene mixed solution, the reaction was carried out at 110 ° C for 4 h; after completion of the reaction, the solution was concentrated and subjected to column chromatography (dichloromethane: ethanol = 100:1, ν / ν) to afford intermediate 8 ((1,E2Ε) -4-((E)-1,3,3-trimethylporphyrin-2-methylene)-N-phenyl-2-propanyl-1-imine).
	In acetonitrile for 12h; Reflux;	1.7; 2.7 7. The synthesis method of TPE-M-Id is as follows: Methyl iodide was added to a solution of 2,3,3-trimethyl-3H-indole in acetonitrile, and the mixture was refluxed for 12h, filtered under reduced pressure, washed with ethyl acetate and dried to give 1, 2, 3 , 3-tetramethyl-3H-indole iodide.
	In acetonitrile Reflux;
	at 50℃; for 4h;	1.2 (2) Synthesis of compound 1,2,3,3-tetramethylindole iodide (6): 0.795 g of 2,3,3-trimethyl-3H-indole (4) (5 mmol) and 0.719 g of methyl iodide (5) (5 mmol) were weighed in a high pressure tube and reacted at 50 ° C for 4 h. After completion of the reaction was rinsed with petroleum ether and suction filtered, dried to give a pale purple solid, iodide 1,2,3,3-tetramethylindole (6);
	In acetonitrile at 80℃; Sealed tube;
	In acetonitrile for 24h; Reflux;
	In toluene at 120℃; for 4h;	1-5 Example 1 Take 2,3,3-trimethylhydrazine 1 (1.43g, 9.00mmol), weigh iodomethane (2.55g, 18.00mmol), weigh 20mL of toluene, mix and dissolve, heat and stir, reflux at 120 ° C for 4 hours The mixture was washed with ethanol to give a red-white solid compound 3. The above compound 3 (301.2 mg, 1 mmol) was weighed, and 2-formylpyrrole (190.2 g, 2.00 mmol) was weighed, and 10 mL of ethanol was weighed, mixed and dissolved, heated and stirred, and refluxed at 80 ° C for 2 hours, dried and dissolved by heating with water. The filtrate was obtained by suction filtration, and then extracted with dichloromethane to give compound 5:
	for 12h;

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2
[ 13673-62-6 ]
[ 5418-63-3 ]
[ 80-40-0 ]
(3-ethyl-benzoxazol-2-yl)-(1,3,3-trimethyl-3<i>H</i>-indol-2-yl)-methinium ; iodide [ No CAS ]

Reference： [1]Patent: US2310640,1934,

3
[ 1805-65-8 ]
[ 74-88-4 ]
[ 5418-63-3 ]

Reference： [1]Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti,1902,vol. <5> 11 II,p. 185

4
[ 2598-30-3 ]
[ 5418-63-3 ]
[ 2240-70-2 ]

Reference： [1]Journal of Organic Chemistry,1964,vol. 29,p. 3450,3451

5
[ 488-11-9 ]
[ 5418-63-3 ]
[ 35542-76-8 ]

Reference： [1]Journal of the Chemical Society,1932,p. 260,265

6
[ 94-31-5 ]
[ 5418-63-3 ]
[ 62783-77-1 ]

Reference： [1]Journal of the Chemical Society,1944,p. 489,491

7
[ 90151-04-5 ]
[ 5418-63-3 ]
3-nitro-4-[2-(1,3,3-trimethyl-indolin-2-yliden)-ethylidene]-cyclohexa-2,5-dienone [ No CAS ]

Reference： [1]Journal of the Chemical Society,1951,p. 3033,3036
Journal of the Chemical Society,1956,p. 1364

8
[ 5418-63-3 ]
[ 6780-49-0 ]
(1,3,3-trimethyl-indolin-2-yliden)-acetaldehyde phenylimine; hydriodide [ No CAS ]

Reference： [1]Journal of the Chemical Society,1947,p. 954,956

9
[ 16644-30-7 ]
[ 5418-63-3 ]
[ 38147-35-2 ]

Reference： [1]Bulletin de la Societe Chimique de France,1979,vol. <II>,p. 315 - 324

10
[ 36404-89-4 ]
[ 5418-63-3 ]
[ 138060-93-2 ]

Reference： [1]Journal of the American Chemical Society,1992,vol. 114,p. 778 - 780

11
[ 27428-79-1 ]
[ 5418-63-3 ]
[ 104989-11-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide With cholin hydroxide In water at 80℃; for 0.333333h; Green chemistry; Stage #2: 1-nitroso-naphthalene-2,7-diol In water at 80℃; for 0.666667h; Green chemistry;	General method for the synthesis of spironaphthoxazines General procedure: A mixture of indolium iodide 1 (1.0 mmol) and choline hydroxide (10 mol %) in water (3 mL) was stirred at 80 °C for 20 min. Then 1-nitroso-2-naphthol 2 (1.0 mmol) was added and the resulting mixture stirred at 80°C for another 40 min. Then reaction mass was cooled to rt. The solid product was then filtered and washed with water. The synthesized product was finally purified using column chromatography technique (silica gel 100-200 mesh size) with ethyl acetate:hexane (05:95) as an eluent to give the desired spironaphthoxazine (Scheme 2 & Table 1).
50%	With triethylamine In ethanol for 2h; Heating;
42%	With triethylamine In isopropyl alcohol for 2h; Heating;

37%

With triethylamine In ethanol for 2h; Heating;

Reference： [1]Vajekar, Shailesh N.; Shankarling, Ganapati S. [Synthetic Communications, 2020, vol. 50, # 3, p. 338 - 347]
[2]Kakishita, Tomonari; Matsumoto, Kiyoichi; Kiyotsukuri, Tsuyoshi; Matsumura, Kenji; Hosoda, Masahiro [Journal of Heterocyclic Chemistry, 1992, vol. 29, # 7, p. 1709 - 1715]
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12
[ 5418-63-3 ]
[ 118-12-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium hydroxide In water at 20℃; for 4h;	1-2 Example 1-2: Synthesis of Intermediate 2 compound An aqueous sodium hydroxide solution (10 wt%) was added to Intermediate 1 (0.09 mol), followed by stirring at room temperature for 4 hours.After the reaction was completed, the organic layer obtained after separation of the reaction mixture and dichloromethane was dried over magnesium sulfate, and the solvent was removed using a rotary evaporator to obtain a mixture containing the intermediate 2 compound as a red liquid in a yield of 90%. .
71%	With sodium hydroxide In diethyl ether; water for 0.5h;
55%	With potassium hydroxide at 20℃; for 1h;

	With potassium hydroxide Ambient temperature;
	With sodium hydroxide
	With potassium hydroxide In water; toluene
	With sodium hydroxide at 20℃;
	With sodium hydroxide In diethyl ether
	Multi-step reaction with 2 steps 1: durch Destillation im Kohlensaeurestrom oder im Vakuum 2: 100 °C
	With potassium hydroxide	2 EXAMPLE 2 EXAMPLE 2 In an aqueous solution of potassium hydroxide (0.7 mol/l, 107 mmol) was suspended 1,2,3,3-tetramethylindolenium iodide (1.5133 g, 5.03 mmol) and the suspension was stirred at room temperature for 1 hour, whereby a yellow oil was produced in the reaction system. This oil was extracted with diethyl ether and the extract was washed with saturated aqueous sodium chloride solution until a neutral aqueous wash was obtained. Then, the extract was dried by addition of anhydrous sodium sulfate and the ether was distilled off to give 1,3,3-trimethyl-2-methyleneindoline as a red liquid. Yield 807.2 mg, 93% 1 H-NMR (CDCl3): 6ppm 1.3 (s, 6H, 3-CH3), 3.1 (s, 3H, N-CH3), 4.0 (s, 2H, =CH2), 6.5-7.2 (m, 4H, aromatic H)
	With sodium hydroxide In water; acetone	1 Preparation of compound 3: After the crude solid of compound 2 is washed with acetone, a portion of the solid is dissolved in NaOH aqueous solution (1 M). The resultant 1,3,3-trimethyl-2-methyleneindoline is extracted with chloroform. The organic layer is dried with anhydrous Na2SO4 and the solvent was evaporated.
	With sodium carbonate In water at 20℃;	General procedure: To a stirred solution of the corresponding iodide (5a-c, 5 mmol) in distilled water (15 mL), sodium carbonate (1.06 g, 10 mmol) was added at rt. The mixture became turbid and was extracted with diethyl ether (3*20 mL). The combined organic phase was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to afford the corresponding 2-methylidene-2,3-dihydro-1H-indole (6a, 6b, and 6c, respectively) as an oil.
	With sodium hydroxide In water	1 Preparation of Compound 3: Preparation of Compound 3: [0111] After the crude solid of compound 2 is washed with acetone, a portion of the solid is dissolved in NaOH aqueous solution (1 M). The resultant 1,3,3-trimethyl-2-methyleneindoline is extracted with chloroform. The organic layer is dried with anhydrous Na2SO4 and the solvent was evaporated.
	With sodium carbonate In water at 20℃; for 0.0166667h;
	With sodium hydroxide In diethyl ether for 0.5h;	1 Manufacturing example 1 4 g (13.28 mol) of the compound 1c was dissolved in 320 ml of diethyl ether: 2M NaOH = 1: 3 and stirred for 30 minutes. The organic layer was passed through MgSO4,solvent was removed under reduced pressure. 3 g (17.32 mmol, 1 eq) of the compound 1d,was dissolved in 30 ml of MC and the solution dissolved in 35 ml of MC ((Chloroethylene) dimethyliminium chloride) 2.5 g (1.953 mol, 1.13 eq) was slowly added. After stirring for 15 minutes, 75 ml of 10% aqueous NaOH solution in an ice bath was slowly added. The mixture was stirred for 1 hour and 30 minutes, and the organic layer was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and used in the next reaction without further separation.
	With triethylamine In ethanol at 70℃; for 1h;	3 7-hydroxy-2-mercaptonaphthalene (Compound 4c, 1.76 g, 10 mmol) was completely dissolved in 21 mL of a 1.2 mol / L aqueous solution of sodium hydroxide,The system was cooled to -5 ° C using an ice bath,And keep low temperature conditions.NaNO2 (828 mg, 12 mmol) was added to the system to complete dissolution.Subsequently, 6 g of dilute sulfuric acid at a concentration of 45% was slowly added under constant stirring,Add after the low temperature stirring 1 hour, after filtration,Wash the filter cake into a neutral vacuum and then dry,The intermediate product (6c) was obtained.The newly prepared N-methyl iodide (compound 5c, 3.01 g, 10 mmol) was then added to a flask containing 40 mL of absolute ethanol,After adding triethylamine (3 mL), the mixture was heated at 70 ° C for 1 hour to give the intermediate product (5c ').While the reaction was carried out in the intermediate (5c), the intermediate product (6c) (compound 6c, 2.46 g, 12 mmol) was added to another flask containing 60 mL of absolute ethanol and heated at 70 ° C.After 1 hour, the solution in the flask containing the intermediate (6c) was added dropwise to another flask containing the intermediate (5c '), heating was continued, and the reaction was monitored by thin layer chromatography (TLC) until the reaction was completed.
	With sodium hydroxide at 20℃; for 0.166667h;	1.b b) Synthesis of 1,3,3-trimethyl-2-methyleneindolinine (7): 1,2,3,3-tetramethyl-3H-indol-1-ium iodide (2 g, 6.63 mmol) was dissolved in a stirred 40% of 10 NaOH (60 mL) and 11 diethyl ether (150 mL) was added into the reaction mixture vigorous and stirred at 25-30° C. for 15-30 mis. After this period of time diethyl ether was separated and dried with anhydrous sodium sulphate. It was filtrated and evaporated under reduced pressure. The yield of 12 compound was yellow oil in nature. It was characterized by 1H-NMR by using CDCl3 solvent it was given below (δ,ppm., J(Hz)): J=1.27 (6H, s, (CH3)2); J=4.31(3H, s, (CH3); J=2.96 (3H, s, N-CH3); J=6.44 (1H d, CH); J=6.68 (1H, t, CH); J=6.72-7.18 (2H, m, CH).
	With piperidine In butanone for 0.0833333h; Reflux; Inert atmosphere;

Reference： [1]Current Patent Assignee: UKSEUNG CHEMICAL CO LTD - KR2021/42029, 2021, A Location in patent: Paragraph 0107; 0113-0115
[2]Natali, Manuel; Giordani, Silvia [Organic and Biomolecular Chemistry, 2012, vol. 10, # 6, p. 1162 - 1171]
[3]Hirano, Masafumi; Osakada, Kohtaro; Nohira, Hiroyuki; Miyashita, Akira [Journal of Organic Chemistry, 2002, vol. 67, # 2, p. 533 - 540]
[4]Hirano, Masafumi; Miyashita, Akira; Nohira, Hiroyuki [Chemistry Letters, 1991, # 2, p. 209 - 212]
[5]Arakawa, Sei'ichi; Kondo, Hirofumi; Seto, Jun'etsu [Chemistry Letters, 1985, p. 1805 - 1808] Traven; Miroshnikov; Chibisova; Barachevsky; Venidiktova; Strokach [Russian Chemical Bulletin, 2005, vol. 54, # 10, p. 2417 - 2424]
[6]Henning, Hans-Georg; Thanh, Le Hoang; Laue, Joerg; Urban, Barbara; Reck, Guenter [Monatshefte fur Chemie, 1994, vol. 125, # 1, p. 95 - 106]
[7]Tan, Ting-Feng; Chen, Pei-Li; Huang, Hua-Ming; Meng, Ji-Ben [Tetrahedron, 2005, vol. 61, # 34, p. 8192 - 8198]
[8]Roxburgh, Craig J.; Sammes, Peter G. [European Journal of Organic Chemistry, 2006, # 4, p. 1050 - 1056]
[9]Ciamician; Boeris [Gazzetta Chimica Italiana, 1894, vol. 24 II, p. 301][Gazzetta Chimica Italiana, 1897, vol. 27 I, p. 78]
[10]Current Patent Assignee: OTSUKA HOLDINGS CO LTD - US5288592, 1994, A
[11]Current Patent Assignee: KOREA UNIVERSITY - US2011/198546, 2011, A1 Location in patent: Page/Page column 12
[12]Dagiliene, Migle; Martynaitis, Vytas; Vengris, Mikas; Redeckas, Kipras; Voiciuk, Vladislava; Holzer, Wolfgang; Šačkus, Algirdas [Tetrahedron, 2013, vol. 69, # 44, p. 9309 - 9315]
[13]Current Patent Assignee: KOREA UNIVERSITY - US2014/191168, 2014, A1 Location in patent: Paragraph 0110-0111
[14]Dagiliene, Migle; Martynaitis, Vytas; Kriščiu¯niene, Vilija; Krikštolaityte, Sonata; Šačkus, Algirdas [ChemistryOpen, 2015, vol. 4, # 3, p. 363 - 369]
[15]Current Patent Assignee: LG CHEM CO.,LTD. - KR2016/22280, 2016, A Location in patent: Paragraph 0166; 0174-0176
[16]Current Patent Assignee: Institute of Chemistry (in: CAS); CHINESE ACADEMY OF SCIENCES - CN104130269, 2017, B Location in patent: Paragraph 0082; 0083; 0086
[17]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - US2018/163053, 2018, A1 Location in patent: Paragraph 0061; 0063
[18]Ajiro, Hiroharu; Ando, Tsuyoshi; Murase, Nobuo [Journal of Materials Chemistry B, 2020, vol. 8, # 7, p. 1489 - 1495]

13
[ 5418-63-3 ]
[ 148-53-8 ]
[ 13433-31-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).
54%	With piperidine In isopropyl alcohol for 2h; Heating;

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]
[2]Chernyshev; Chernov'yants; Voloshina; Voloshin [Russian Journal of General Chemistry, 2002, vol. 72, # 9, p. 1468 - 1472]

14
[ 2892-62-8 ]
[ 5418-63-3 ]
3-butoxy-4-(1,3,3-trimethyl-2,3-dihydro-1H-indol-2-ylidenemethyl)-cyclobut-3-ene-1,2-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With triethylamine; In butan-1-ol; at 70℃; for 1h;Inert atmosphere;	General procedure: The corresponding indolium iodide (1 equiv.) and 3, 4-dibutoxycyclobut-3-ene-l,2-dione (1 equiv) were dissolved in 1-butanol in a 50 mL two necked round bottomed flask and triethylamine (1.2 equiv) was added into the reaction mixture. The reaction mixture was heated at 70 C for 1 h under nitrogen atmosphere. The reaction mixture cooled to room temperature, and the solvents were removed under reduced pressure. The reaction mixture was purified by column chromatography (Si02, 100-200 mesh) 5% EtOAc and 95% petroleum ether to afford the required compound as a yellow solid. (0114) (E)-2-((2-butoxy-3,4-dioxocyclobut-l-en-l-yl)methylene)-l,3,3-trimethyl-indoline (8): 1.6g, Yield: 74 %; 1H NMR (CDC13, 200MHz) delta: 7.29-724 (m, 2H), 7.07 (t, /=7.4Hz, IH), 6.88 (d, /=7.24Hz, IH), 5.36 (s, IH), 4.85 (t, /=6.6Hz, 2H), 3.37 (s, 3H), 1.95-1.79 (m, 2H), 1.61 (s, 6H), 1.58- 1.42(m, 2H), 1.01(t, /=7.2Hz, 3H); 13C NMR (CDCI3, 50 MHz) delta: 192.7, 187.5, 173.5, 168.3, 142.6, 140.9, 127.7, 122.6, 121.9, 108.4, 81.2, 73.7, 47.9, 43.0, 32.1, 31.4, 26.9, 26.6, 26.2, 22.4, 18.7, 13.9, 13.7; HRMS (m/z): [M + H]+ calcd for C20H24NO3: 326.1751 ;found: 327.1570; [M + Na]+ calcd for C20H23NO3Na: 348.1570; found: 348.1569.

Reference： [1]Journal of Structural Chemistry,2005,vol. 46,p. 154 - 158
[2]Patent: WO2018/20518,2018,A1 .Location in patent: Page/Page column 23; 24

15
[ 5418-63-3 ]
[ 114747-45-4 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 8192 - 8198

16
[ 5418-63-3 ]
[ 114747-44-3 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 8192 - 8198

17
[ 5418-63-3 ]
[ 114747-48-7 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 8192 - 8198

18
[ 5418-63-3 ]
[ 62473-58-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With ammonium hexafluorophosphate In water; acetone for 1h;	A solution of NH4PF6 (0.75 g, 5 mmol) in H2O (5 ml_) was added to a solution of the iodide salt of 6 (1.38 g, 5 mmol) in Me2CO (30 ml_). The mixture stirred for 1 h, concentrated to ca. 10 ml_ under reduced pressure and cooled down to 5°C. The resulting precipitate was filtered to give the hexafluorophosphate salt of 6 (95%, 1.40 g) as a pink solid.

Reference： [1]Current Patent Assignee: UNIVERSITY OF MIAMI - WO2009/51820, 2009, A2 Location in patent: Page/Page column 9; 3/3

19
[ 5418-63-3 ]
[ 108-24-7 ]
[ 1497-49-0 ]
[ 24136-79-6 ]

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 51 - 55

20
[ 5418-63-3 ]
[ 97-51-8 ]
[ 1498-88-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With cholin hydroxide; In water; at 80℃; for 1h;Green chemistry;	General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).
91%		1,2,3,3-Tetramethylindolindolenium iodide (6.35 g, 21 mmol)was dissolved in anhydrous methanol (100 mL) and heated toreflux. Then triethylamine (1 mL) was added and the solution wasstirred for 15 min. 5-Nitrosalicylaldehyde (3.34 g, 20 mmol) wasadded and the mixture was refluxed for 2 h. After reaction themixture was allowed to cool to room temperature and methanolwas removed by evaporation. The formed orange solid wasrecrystallized with dichloromethane/ethanol. Yellow solid (5.88 g)of the target product 1,3,3-trimethyl-60-nitrospiro[chromene-2,20-indoline] was obtained in 91% yield after filtration and drying. Mp178e180 C (literature [64] value: 178e179 C). 1H NMR (400 MHz,CDCl3) d 8.05e8.03 (m, 2H), 7.25e7.23 (m, 1H), 7.12 (dd, J 7.3,1.3 Hz, 1H), 6.99e6.88 (m, 2H), 6.80 (d, J 8.6 Hz, 1H), 6.59 (d,J 7.7 Hz, 1H), 5.89 (d, J 10.3 Hz, 1H), 2.77 (s, 3H),1.32 (s, 3H),1.22(s, 3H).

Reference： [1]Synthetic Communications,2018,vol. 48,p. 208 - 215
[2]Journal of Molecular Structure,2020,vol. 1204
[3]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7245 - 7254
[4]Physical Chemistry Chemical Physics,2010,vol. 12,p. 13737 - 13745
[5]ChemistryOpen,2018,vol. 7,p. 520 - 526

21
[ 5418-63-3 ]
[ 57597-64-5 ]
[ 1352626-59-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	In ethanol for 12h; Reflux;
56%	In ethanol for 5h; Reflux; Inert atmosphere;
56%	In ethanol Reflux;	2 General procedure: The synthetic indole salt derivative (MR) 1.0mmol and coumarin aldehyde derivative 1.0mmol were dissolved in 20mL ethanol solution.After heating and refluxing for 12h, the solvent was spin-dried under reduced pressure after completion of the reaction. The resulting residue was separated by column chromatography (CH2Cl2: CH3OH, 0: 1 to 10: 1),The corresponding CMC series products are obtained.

47%	In ethanol at 60℃; for 20h;
	With acetic acid In ethanol
	In ethanol at 75℃; for 5h;

Reference： [1]Lv, Xin; Liu, Jing; Liu, Yunlong; Zhao, Yun; Sun, Yuan-Qiang; Wang, Pi; Guo, Wei [Chemical Communications, 2011, vol. 47, # 48, p. 12843 - 12845]
[2]Fang, Hongbao; Chen, Yuncong; Shi, Xiangchao; Bai, Yang; Chen, Zhongyan; Han, Zhong; Zhang, Yuming; He, Weijiang; Guo, Zijian [New Journal of Chemistry, 2019, vol. 43, # 37, p. 14800 - 14805]
[3]Current Patent Assignee: NANJING UNIVERSITY - CN110804043, 2020, A Location in patent: Paragraph 0026; 0030-0032
[4]Shiraishi, Yasuhiro; Nakamura, Masaya; Yamamoto, Kohei; Hirai, Takayuki [Chemical Communications, 2014, vol. 50, # 78, p. 11583 - 11586]
[5]Zha, Jiayu; Fu, Boqiao; Qin, Caiqin; Zeng, Lintao; Hu, Xichao [RSC Advances, 2014, vol. 4, # 81, p. 43110 - 43113]
[6]Tirla, Alina; Rivera-Fuentes, Pablo [Chimia, 2018, vol. 72, # 4, p. 241 - 244]

22
[ 1354932-51-6 ]
[ 5418-63-3 ]
[ 1354932-52-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine; acetic anhydride at 50℃; for 18h;	6.2. Synthesis of 2-[3-(1-Butyl-2,3-dihydro-3,3-dimethyl-5-iodo-1H-indol-2-ylidene)-1-propenyl]-1,3,3-trimethyl-3HindoliumIodide (15) Hemicyanine 14 (2.84 g, 4.97 mmol, 1 eq) and 1,2,3,3-tetramethyl-3H-indolium iodide 1 (2.25 g, 7.46 mmol, 1.5 eq) were suspended in anhydrous pyridine (25 mL) and then acetic anhydride (4.7 mL) was added. The reaction mixture was stirred at 50 °C for 18 h, then cooled to room temperature and precipitated with cold diethyl ether. The precipitate was filtered off and washed with diethyl ether. Column chromatography (5 % MeOH/EtOAC) afforded the product 15 in 95 % yield (3.10 g, 4.74 mmol). Mw = 652.39 g/mol (C28H34I2N2).

Reference： [1]Gerowska, Marta; Hall, Lucy; Richardson, James; Shelbourne, Montserrat; Brown, Tom [Tetrahedron, 2012, vol. 68, # 3, p. 857 - 864]

23
[ 5418-63-3 ]
[ 1498-88-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 1162 - 1171

24
[ 4181-05-9 ]
[ 5418-63-3 ]
[ 572914-85-3 ]

Yield	Reaction Conditions	Operation in experiment
48.2%	With piperidine In ethanol at 80℃; for 12h; Reflux; Inert atmosphere;	Synthesis of TPA-1 A solution of 4-formyltriphenylamine(5, 0.3 g, 1.1 mmol), 1,2,3,3-tetramethyl-3H-indoliumiodide (1, 0.34 g,1.1 mmol) and 5 drops piperidine in anhydrous ethanol (60 mL) was refluxed for12 h under nitrogen with stirring. After cooling to room temperature, thesolvent was evaporated under reduced pressure. The residuewas purified by column chromatography on silica gel eluting with CH2Cl2/CH3OH(20:1, v/v) to afford TPA-1 (0.31 g,48.2 %) as a dark purple solid. 1H NMR(400MHz, CDCl3) δ: 8.11 (d, J=15.7Hz, 1H), 8.00 (d, J=8.9 Hz, 2H),7.53-7.46 (m, 5H), 7.36-7.32 (m, 4H), 7.22-7.15 (m, 6H), 6.98 (s, 1H), 6.96 (s,1H), 4.28 (s, 3H), 1.79 (s, 6H). 13C NMR (100 MHz, CDCl3) δ: 180.62, 154.33,153.98, 145.20, 142.42, 141.69, 134.10, 129.93, 129.46, 128.74, 126.70, 126.12,125.98, 122.47, 119.22, 113.84, 108.22, 51.63, 36.41, 29.68, 27.39; LC-MS: (positive mode, m/z)calculated 429.2325, found 429.2322 for [M-I]+.
	In ethanol for 24h; Reflux;

Reference： [1]Wang, Ming-Qi; Zhu, Wen-Xiang; Song, Zhuan-Zhuan; Li, Shuo; Zhang, Yong-Zhao [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 24, p. 5672 - 5676]
[2]Location in patent: experimental part Deniz, Erhan; Cusido, Janet; Swaminathan, Subramani; Battal, Mutlu; Impellizzeri, Stefania; Sortino, Salvatore; Raymo, Françisco M. [Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 229, # 1, p. 20 - 28]

25
[ 5418-63-3 ]
[ 1761-61-1 ]
[ 16650-14-9 ]

Yield	Reaction Conditions	Operation in experiment
87%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).
77%	With triethylamine In ethanol for 2h; Sonication; Inert atmosphere;
	Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide; 5-bromosalicyclaldehyde In ethanol at 78℃; Stage #2: With sodium hydroxide

Multi-step reaction with 2 steps 1: ethanol / 0.67 h / Sonication 2: sodium carbonate / acetonitrile

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]
[2]Location in patent: experimental part Barrois, Sebastian; Beyer, Christoph; Wagenknecht, Hans-Achim [Synlett, 2012, vol. 23, # 5, p. 711 - 716]
[3]Qi, Qingkai; Qian, Jingyu; Ma, Suqian; Xu, Bin; Zhang, Sean Xiao-An; Tian, Wenjing [Chemistry - A European Journal, 2015, vol. 21, # 3, p. 1149 - 1155]
[4]Colaço, Melwin; Carletta, Andrea; Van Gysel, Mégane; Robeyns, Koen; Tumanov, Nikolay; Wouters, Johan [ChemistryOpen, 2018, vol. 7, # 7, p. 520 - 526]

26
[ 3328-70-9 ]
[ 5418-63-3 ]
[ 108-24-7 ]
[ 1384511-92-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With sodium acetate; In acetic anhydride; at 80℃; for 0.5h;Inert atmosphere;	Preparation of Compound 3: A mixture of commercially available Compound 2 (50 mg, 0.33 mmol), NaOAc (83.9 mg, 1.02 mmol), and commercially available l,2,3,3-tetramethyl-3H-indolium iodide (210.6 mg, 0.70 mmol) was dissolved in 2 ml Ac20. The reaction mixture stirred for 30 minutes at 80 C under an Ar atmosphere and monitored by RP-HPLC (grad. 10 %-90 ACN in water, 20 minutes). After completion, the solvent was evaporated under reduced pressure, and the crude product was dissolved in DCM, filtered and concentrated to give compound 3 (210 mg) as a red solid.1H NMR (400MHz, CDC13 + drope of MeOD): delta = 9.63 (1H, s), 8.67 (1H, d, J=16.4 Hz), 8.52 (1H, d J=8.6 Hz), 8.27 (2H, m), 8.05 (1H, d, J=16.4 Hz), 7.62-7.70 (8H, m), 7.52 (1H, d, J=8.6 Hz), 4.54 (3H, s), 4.48 (3H, s), 2.49 (3H, s), 1.98 (6H, s), 1.88 (6H, s).13C NMR (400MHz, CDC13 + drope of MeOD): delta = 183.89, 183.32, 186.77, 154.20, 152.68, 145.82, 144.41, 143.96, 142.03, 136.88, 133.39, 133.23, 131.40, 131.05, 130.56, 130.25, 127.94, 127.94, 124.73, 123.48, 117.40, 115.93, 115.58, 115.53, 53.85, 53.52, 38.40, 37.92, 30.31, 27.38, 27.12, 27.12, 21.93, 0.57.MS (ESI): m/z calc. for C34H36N2022+: 252.2 ; found: 252.2 [M]+.

Reference： [1]Patent: WO2012/123916,2012,A2 .Location in patent: Page/Page column 63-64

27
[ 2892-62-8 ]
[ 5418-63-3 ]
[ 357657-11-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With triethylamine; In butan-1-ol; at 75℃; for 0.3h;	General procedure: An alcohol solution (11, 13, 15: BuOH; 12, 14: EtOH, 12 mL) of a 2,3,3-trimethyl-3H-indolium iodide 5-7 (8 mmol), a 3,4-dialkoxycyclobut-3-ene-1,2-dione 8-10 (8 mmol), and triethylamine (1.6 mL) was heated at 75 C (11: 0.3 h; 12, 14: 2 h; 13, 15: 1 h). After the reaction was completed, to the mixture were added water (20 mL) and dichloromethane (50 mL). The dichloromethane layer was separated, washed with water (50 mL×3), and dried over anhydrous sodium sulfate. The solvent was removed in vacuo. The product was purified by silica gel column chromatography (CH2Cl2 then CH2Cl2/AcOEt=20:1) and recrystallized from hexane.

Reference： [1]Tetrahedron,2012,vol. 68,p. 9936 - 9941,6
[2]Dyes and Pigments,2017,vol. 147,p. 120 - 129

28
[ 5418-63-3 ]
[ 100-10-7 ]
[ 6307-03-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	In ethanol for 4.5h; Inert atmosphere; Reflux;
87%	In ethanol for 12h; Reflux; Inert atmosphere;	Synthesis of H The dye H was synthesized according to thereported procedure (28).1 (301.17 mg, 1.0 mmol) and 4-dimethylaminobenzaldehyde(179.028 mg, 1.2 mmol) were dissolved inethyl alcohol (40 mL). The solution was stirred at refluxunder an inert nitrogen atmosphere for 12 h. On cooling,the resulting solution was filtered and the kermesinus-like precipitate was washed with diethyl ether andthen dried in vacuum to give H (376.14 mg,87%).1H NMR (D2O, 400 MHz,) δ 8.04 (d, J = 15.7 Hz,1H), 7.66 (d, J = 9.0 Hz, 2H), 7.46 (d, J = 7.2 Hz, 1H),7.39-7.28 (m, 3H), 6.91 (d, J = 15.6 Hz, 1H), 6.70 (d, J =9.0 Hz, 2H), 3.69 (s, 3H), 2.95 (s, 6H), 1.57 (s, 6H), (FigureS2). And MALDI-TOF MS spectra are shown in Figure S3.
100.8 mg	In ethanol for 12h; Reflux; Inert atmosphere;	General methods for the synthesis of 2-styrylindolium derivatives General procedure: A mixture of 1-alkyl-2,3,3-trimethyl-3H-indolium iodide (0.25 mmol, 1.0 eq) and the corresponding aldehyde (0.275 mmol, 1.1 eq) was dissolved in EtOH (10 mL), and then heated with reflux for 12 h under nitrogen. The solvent was evaporated in vacuo. The crude product was purified by column chromatography (SiO2; CH2Cl2/MeOH 10:1) to afford colourful 2-styrylindolium derivatives as solid. The derivatives were unstable in high temperature that no melting points were provided.

Reference： [1]Li, Dong-Peng; Wang, Zhao-Yang; Cao, Xiang-Jian; Cui, Jie; Wang, Xin; Cui, Hao-Zhong; Miao, Jun-Ying; Zhao, Bao-Xiang [Chemical Communications, 2016, vol. 52, # 13, p. 2760 - 2763]
[2]Xu, Weitao; Kan, Jinglan; Redshaw, Carl; Bian, Bing; Fan, Ying; Tao, Zhu; Xiao, Xin [Supramolecular Chemistry, 2019, vol. 31, # 7, p. 457 - 465]
[3]Gu, Jiamin; Anumala, Upendra Rao; Lo Monte, Fabio; Kramer, Thomas; Heyny Von Haussen, Roland; Hoelzer, Jana; Goetschy-Meyer, Valerie; Mall, Gerhard; Hilger, Ingrid; Czech, Christian; Schmidt, Boris [Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7667 - 7671]

29
[ 1415799-08-4 ]
[ 5418-63-3 ]
4-[(1,3,3-trimethylindol-1-ium-2-yl)methylidene]-2-(3-methylimidazo[1,5-a]pyridin-1-yl)-3-oxocyclobut-1-en-1-olate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With pyridine In butan-1-ol for 5h; Reflux;	4-[(1,3,3-Trimethylindol-1-ium-2-yl)methylidene]-2-(3-methylimidazo[1,5-a]pyridin-1-yl)-3-oxocyclobut-1-en-1-olate (6a) A solution of 5 (0.034 g, 0.15 mmol) and 1,2,3,3-tetramethylindolium iodide (0.045 g, 0.15 mmol) in a mixture of butan-1-ol/pyridine (10/1, v/v) (10 mL) was heated under reflux for 5 h. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The resulting residuewas purified by column chromatography (CHCl3/MeOH, 9/1, v/v) to afford 6a (0.038 g, 67%), as a blue solid.MP254e256 C. IR nmax: 632, 756, 796,972,1059,1258,1444,1521,1602, 3415. 1HNMR(CDCl3) d: 1.82 (6H, s,C(CH3)2), 2.74 (3H, s, CH3), 3.73 (3H, s, NCH3), 6.17 (1H, s, CH¼C), 6.87(1H, t, J ¼ 6.5, ArH), 7.13e7.16 (2H, m, ArH), 7.25e7.28 (1H, m, ArH),7.36e7.42 (2H, m, ArH), 7.83 (1H, d, J¼ 7.0, ArH), 9.18 (1H, d, J¼ 9.0,ArH). 13C NMR(CDCl3) d: 12.8, 26.5, 29.6, 31.8, 50.5, 89.3,110.5,115.4,122.1, 122.4, 123.1, 123.7, 124.3,125.5, 128.1, 136.1, 141.2, 142.3, 142.4,170.7, 175.3, 187.5. HRMS (ESI-TOF) m/z: 384.17053 ([Mþ H]þ; calc. for C24H22N3O2: 384.17065).

Reference： [1]Prostota, Yaroslav; Kachkovsky, Oleksiy D.; Reis, Lucinda V.; Santos, Paulo F. [Dyes and Pigments, 2013, vol. 96, # 2, p. 554 - 562]

30
[ 1289218-74-1 ]
[ 5418-63-3 ]
[ 1414838-38-2 ]

Reference： [1]Chemical Communications,2012,vol. 48,p. 12195 - 12197

31
[ 1221163-04-7 ]
[ 5418-63-3 ]
C₂₇H₃₇N₂O₂S₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.7%	In ethanol at 95℃; for 14.3333h; Inert atmosphere;	4 2.4. Preparation of the chemosensor tetrafluoroborate of 2-{2-[4-N,N’-bis(2-hydroxyethylthio-ethyl)aminophenyl]ethenyl}-1,3,3’-trimethylindoline 3 To a 50 mL round-bottomed flask, was charged N-methyl-2,3,3'-trimethylindolium iodide (0.51 g, 1.55 mmol), compound 2 (0.462 g, 1.54 mmol) and ethanol (8 mL). The reaction suspension was flushed with nitrogen for 20 min, and then stirred for 14 h at 95 °C. After cooling, the reaction mixture was condensed to dryness. The residue was purified by column chromatography (SiO2, CH2Cl2/EtOH, 10:1, v/v). The product was obtained as red powder (0.824 g) in 87.7% yield.

Reference： [1]Li, Yuanyuan; Wei, Fangfang; Lu, Yan; He, Song; Zhao, Liancheng; Zeng, Xianshun [Dyes and Pigments, 2013, vol. 96, # 2, p. 424 - 429]

32
[ 528-75-6 ]
[ 5418-63-3 ]
[ 1428133-84-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium acetate; acetic anhydride at 20℃; for 12h;	The DTI probe was synthesized by one step. 2,4-Dinitrobenzaldehyde (0.392 g, 2 mmol) was dissolved in 10 mL of acetic anhydride, then 1,2,3,3- tetramethyl-3H-indolium iodide (0.903 g, 3 mmol) and sodium acetate (0.246 g, 3 mmol) were added. The solution was stirred at room temperature for 12 h followed by the addition of 20 mL of diethyl ether. Brown precipitate was obtained. The precipitate was filtered and washed with cold ethyl acetate three times. Drying the precipitate in vacuum afforded DTI as a reddish-brown product (0.62 g, 65%).

Reference： [1]Li, Yin-Hui; Yang, Jin-Feng; Liu, Chang-Hui; Li, Ji-Shan; Yang, Rong-Hua [Chinese Chemical Letters, 2013, vol. 24, # 2, p. 96 - 98]

33
[ 61010-04-6 ]
[ 5418-63-3 ]
2‐(2‐{2‐chloro‐3‐[2‐(1,3,3‐trimethylindol‐2‐ylidene)ethylidene]cyclohex‐1‐en‐1‐yl}ethenyl)‐1,3,3‐trimethylindol‐1‐ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium acetate; acetic anhydride; at 20℃; for 2h;Inert atmosphere;	2,3,3-trimethyl-3H-indole (3.66 g, 11.66 mmol), compound 1(0.96 g, 5.44 mmol) and sodium acetate (0.47 g, 5.44 mmol) weredissolved in 30 mL acetic anhydride under nitrogen atmosphere.The mixture solvent was stirred for 2 h at room temperature. Thenthe mixture solvents were removed under vacuum. The residualwerewashed with ether to obtain 3.2 g of pure green solid (91%). 1HNMR (500 MHz, CDCl3): delta 8.31 (d, J 14.1 Hz, 2H), 7.40-7.33 (m,4H), 7.24e7.14 (m, 4H), 6.18-6.15 (s, 2H), 3.72 (s, 6H), 2.70 (t,J 6.1 Hz, 4H), 1.97-1.88 (m, 2H), 1.69 (s, 12H); 13C NMR (126 MHz,CDCl3): delta 172.90, 150.67, 144.38, 142.75, 140.89, 128.84, 127.65,125.36, 122.15, 110.88, 101.60, 77.40, 77.15, 76.90, 49.25, 32.69,29.66, 28.08, 26.73, 20.68.
84.26%	In cyclohexane; butan-1-ol; at 100℃; for 8h;Inert atmosphere;	Starting material A (0.86 g, 5 mmol),Starting material B (3.76g, 12.5mmol),24 mL of n-butanol and 12 mL of cyclohexane were added to a 100 mL round bottom flask.Vacuuming and replacing N2 three times,The temperature was raised to 100 C and refluxed for 8 hours.After cooling the reaction solution to room temperature,A large amount of metallic luster green solid is produced in the system, which is suction filtered.Rinse the filter cake with ethyl acetate.Obtained 2.57 g of gold-green solid powder,The yield was 84.26%.
75%	In water; toluene; butan-1-ol; for 10h;Inert atmosphere; Reflux;	The specific process is: adding 1,2,3,3-tetramethyl-3H-iodoindole (1.81g, 6mmol) to a two-necked bottle and2-Chloro-1-formyl-3-hydroxymethylcyclohexene (518 mg, 3 mmol), Connect the water separator and pump it three times.n-Butanol and toluene (30 mL, v/v = 7:3) were added under argon.Then, the reaction was stirred under reflux with argon for 10 h. After completion of the reaction, the solvent was evaporated under reduced pressure to give a crude material. purified with a silica gel column (dichloromethane / 0-2% methanol). The green solid product is 2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indole-2-ylidene)ethylene]-1-cyclohexen-1-yl]vinyl]-1,3,3-trimethylindolium iodide, 75% yield.

75%	In toluene; butan-1-ol; for 10h;Reflux; Inert atmosphere;	Add 1,2,3,3-tetramethyl-3H-iodoindole (1.81 g, 6 mmol) to a two-necked vial and2-Chloro-1-formyl-3-hydroxymethylcyclohexene (518 mg, 3 mmol), attached to a water trap,After pumping three times,n-Butanol and toluene (30 mL, v/v = 7:3) were added under argon.Then, the reaction was stirred under reflux with argon for 10 h.After completion of the reaction, the solvent was evaporated under reduced pressure to give a crude product.After washing with diethyl ether, it was purified by silica gel chromatography (dichloromethane / 0-2% methanol).The green solid product is2-[2-[2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indol-2-ylidene)ethylene]-1-cyclohexen-1-yl]vinyl]-1,3,3-trimethylindolium Iodide,The yield was 75%.
75%	In toluene; butan-1-ol; for 10h;Inert atmosphere; Reflux;	Add 1,2,3,3-tetramethyl-3H-iodoindole (1.81g, 6mmol) to the double-necked flaskAnd 2-chloro-1-formyl-3-hydroxymethylcyclohexene (518 mg, 3 mmol),Connected to the water separator, and pumped for three times,Under argon protection, n-butanol and toluene (30 mL, v / v = 7: 3) were added.Then, the reaction was stirred under reflux for 10 h under the protection of argon.After completion of the reaction, the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was washed with ether and filtered, and then purified by silica gel chromatography (dichloromethane / 0-2% methanol).The green solid product was obtained as 2- [2- [2-chloro-3-[(1,3-dihydro-1,3,3-trimethyl-2H-indole-2-ylidene) ethylene] -1-cyclohexene-1-yl] vinyl] -1,3,3-trimethylindolium iodide,Yield: 75%.

Reference： [1]Dyes and Pigments,2017,vol. 137,p. 293 - 298
[2]Journal of Materials Chemistry B,2018,vol. 6,p. 1449 - 1451
[3]Patent: CN109054428,2018,A .Location in patent: Paragraph 0041; 0056; 0061; 0069; 0070; 0071
[4]Organic and Biomolecular Chemistry,2013,vol. 11,p. 4577 - 4580
[5]Patent: CN109134344,2019,A .Location in patent: Paragraph 0056; 0070-0077
[6]Patent: CN109180555,2019,A .Location in patent: Paragraph 0057; 0071-0078
[7]Patent: CN110642772,2020,A .Location in patent: Paragraph 0056; 0070-0077
[8]Journal of Materials Chemistry B,2017,vol. 5,p. 2002 - 2009
[9]Research on Chemical Intermediates,2014,vol. 40,p. 1469 - 1481
[10]Advanced Functional Materials,2015,vol. 25,p. 2316 - 2325
[11]Patent: CN109810101,2019,A .Location in patent: Paragraph 0060; 0064-0066

34
[ 1440207-67-9 ]
[ 5418-63-3 ]
[ 1440207-56-6 ]

Yield	Reaction Conditions	Operation in experiment
43%	With morpholine In ethanol at 60℃;	4.4. 6-(tert-Butyl)-10,30,30-trimethylspiro[chromene-2,20-indoline]-8-carbaldehyde oxime (4a) General procedure: To a solution of 5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde (20 mg, 0.09 mmol) and N-methyl-2,3,3-trimethylindolenine iodide (35 mg, 0.10 mmol) in anhydrous ethanol (10 mL), morpholine (2 mL) was added dropwise. The reaction mixture was refluxed at 60 °C for overnight. After being cooled to room temperature, part of solvent was removed under reduced pressure. Then the reaction mixture was diluted with water and extracted with ethyl acetate (3x10 mL). The combined organic layers were dried by anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford a crude residue, which was purified by column chromatography (n-hexane/ethyl acetate 100:1) to yield product 4a as purple oil (28 mg, 82% yield).

Reference： [1]Chan, Yim-Pan; Fan, Li; You, Qihua; Chan, Wing-Hong; Lee, Albert W.M.; Shuang, Shaomin [Tetrahedron, 2013, vol. 69, # 29, p. 5874 - 5879]

35
[ 1440207-69-1 ]
[ 5418-63-3 ]
[ 1440207-58-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	With morpholine In ethanol at 60℃;	4.4. 6-(tert-Butyl)-10,30,30-trimethylspiro[chromene-2,20-indoline]-8-carbaldehyde oxime (4a) General procedure: To a solution of 5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde (20 mg, 0.09 mmol) and N-methyl-2,3,3-trimethylindolenine iodide (35 mg, 0.10 mmol) in anhydrous ethanol (10 mL), morpholine (2 mL) was added dropwise. The reaction mixture was refluxed at 60 °C for overnight. After being cooled to room temperature, part of solvent was removed under reduced pressure. Then the reaction mixture was diluted with water and extracted with ethyl acetate (3x10 mL). The combined organic layers were dried by anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford a crude residue, which was purified by column chromatography (n-hexane/ethyl acetate 100:1) to yield product 4a as purple oil (28 mg, 82% yield).

Reference： [1]Chan, Yim-Pan; Fan, Li; You, Qihua; Chan, Wing-Hong; Lee, Albert W.M.; Shuang, Shaomin [Tetrahedron, 2013, vol. 69, # 29, p. 5874 - 5879]

36
[ 1440207-70-4 ]
[ 5418-63-3 ]
[ 1440207-60-2 ]

Yield	Reaction Conditions	Operation in experiment
50%	With morpholine In ethanol at 60℃;	4.4. 6-(tert-Butyl)-10,30,30-trimethylspiro[chromene-2,20-indoline]-8-carbaldehyde oxime (4a) General procedure: To a solution of 5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde (20 mg, 0.09 mmol) and N-methyl-2,3,3-trimethylindolenine iodide (35 mg, 0.10 mmol) in anhydrous ethanol (10 mL), morpholine (2 mL) was added dropwise. The reaction mixture was refluxed at 60 °C for overnight. After being cooled to room temperature, part of solvent was removed under reduced pressure. Then the reaction mixture was diluted with water and extracted with ethyl acetate (3x10 mL). The combined organic layers were dried by anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford a crude residue, which was purified by column chromatography (n-hexane/ethyl acetate 100:1) to yield product 4a as purple oil (28 mg, 82% yield).

Reference： [1]Chan, Yim-Pan; Fan, Li; You, Qihua; Chan, Wing-Hong; Lee, Albert W.M.; Shuang, Shaomin [Tetrahedron, 2013, vol. 69, # 29, p. 5874 - 5879]

37
[ 1440207-76-0 ]
[ 5418-63-3 ]
[ 1440207-62-4 ]

Yield	Reaction Conditions	Operation in experiment
56%	With morpholine In ethanol at 60℃;	6-(tert-butyl)-1',3',3'-trimethylspiro[chromene-2,2'-indoline]-8-carbaldehyde O-benzyl oxime (5) A solution of 3-(((benzyloxy)imino)methyl)-5-(tert-butyl)-2-hydroxybenzaldehyde (24 mg, 0.08 mmol) (3e) and 1,2,3,3-tetramethyl-3H-indolium iodide (35 mg, 0.10 mmol) in anhydrous ethanol (10 mL) was added with morpholine (2 mL) dropwisely. The reaction mixture was refluxed at 60 for overnight. After being cooled to room temperature, part of solvent was removed under reduced pressure. Then the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 10 mL). The organic layers were dried by anhydrous sodium sulphate and filtered. The filtrate was evaporated under vacuum to afford a crude residue that was purified by column chromatography (n-hexane/ethyl acetate 100:1) to yield product 5 (20 mg, 56% yield) in oil form with purple colour. 1HNMR (CDCl3-d1) δ (ppm): 1.15 (s, 3H), 1.26 (s, 3H), 1.31 (s, 9H), 2.70 (s, 3H), 5.12 (s, 2H), 5.68 (d, 1H, J=10.2 Hz), 6.48 (d, 1H, J=7.7 Hz), 6.78-6.84 (m, 2H), 7.02 (d, 1H, J=6.3 Hz), 7.08 (d, 1H, J=2.4 Hz), 7.13 (dt, 1H, J=7.6, 1.2 Hz), 7.29-7.41 (m, 5H), 7.67 (d, 1H, J=2.4 Hz), 8.17 (s, 1H). 13CNMR (CDCl3-d1) δ (ppm): 20.5, 26.1, 28.9, 31.4, 34.2, 51.8, 76.4, 104.8, 106.7, 117.4, 118.8, 119.2, 119.9, 121.5, 122.8, 125.7, 127.6, 128.0, 128.1, 128.4, 128.5, 128.6, 129.4, 136.4, 137.3, 142.6, 144.2, 147.9, 150.3, 153.6. HRMS (MALDI-TOF) for C31H34N2O2 calcd 467.2969 (M + H+), found 467.2945.

Reference： [1]Chan, Yim-Pan; Fan, Li; You, Qihua; Chan, Wing-Hong; Lee, Albert W.M.; Shuang, Shaomin [Tetrahedron, 2013, vol. 69, # 29, p. 5874 - 5879]

38
[ 1440207-64-6 ]
[ 5418-63-3 ]
[ 1440207-54-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With morpholine In ethanol at 60℃;	4.4. 6-(tert-Butyl)-10,30,30-trimethylspiro[chromene-2,20-indoline]-8-carbaldehyde oxime (4a) To a solution of 5-(tert-butyl)-2-hydroxy-3-((hydroxyimino)methyl)benzaldehyde (20 mg, 0.09 mmol) and N-methyl-2,3,3-trimethylindolenine iodide (35 mg, 0.10 mmol) in anhydrous ethanol (10 mL), morpholine (2 mL) was added dropwise. The reaction mixture was refluxed at 60 °C for overnight. After being cooled to room temperature, part of solvent was removed under reduced pressure. Then the reaction mixture was diluted with water and extracted with ethyl acetate (3x10 mL). The combined organic layers were dried by anhydrous sodium sulfate and filtered. The filtrate was evaporated under vacuum to afford a crude residue, which was purified by column chromatography (n-hexane/ethyl acetate 100:1) to yield product 4a as purple oil (28 mg, 82% yield). H NMR (CDCl3-d1) δ (ppm): 1.16 (s, 3H), 1.28 (s, 12H), 2.71 (s, 3H), 5.70(d, 1H, J=10.2 Hz), 6.50 (d, 1H, J=7.7 Hz), 6.81 (dd, 1H, J=7.2 Hz), 6.83 (d, 1H, J=10.2 Hz), 7.04 (d, 1H, J=7.1 Hz), 7.09 (d, 1H, J=1.9 Hz), 7.15 (dd, 1H, J=7.5, 7.7 Hz), 7.59 (d, 1H, J=1.9 Hz), 7.97 (br s, 1H), 8.18 (s, 1H). C NMR (CDCl3-d1) δ (ppm): 20.5, 25.9, 28.9, 31.4, 34.1, 51.8, 104.9,106.8,117.2,118.8,119.3,120.0,121.5,122.5,125.8,127.6,129.4, 136.4, 142.7, 145.6, 147.9, 150.4. HRMS (MALDI-TOF) for C24H28N2O2 calcd 377.2223 (M+H+), found, 377.2230.

Reference： [1]Chan, Yim-Pan; Fan, Li; You, Qihua; Chan, Wing-Hong; Lee, Albert W.M.; Shuang, Shaomin [Tetrahedron, 2013, vol. 69, # 29, p. 5874 - 5879]

39
[ 5418-63-3 ]
[ 13959-24-5 ]
[ 19764-96-6 ]

Yield	Reaction Conditions	Operation in experiment
41%	With acetic anhydride; triethylamine In methanol at 20℃; for 16.5h; Darkness; Inert atmosphere;	2.3.1. 1,1',3,3,3',3'-Hexamethylindotricarbocyanine iodide (1) Triethylamine (190 mL, 1.36 mmol) was added to a mixture of 1,2,3,3-tetramethyl-3H-indolium iodide (211 mg, 0.70 mmol), N-(5-anilino-2,4-pentadienylidene)aniline hydrochloride (100 mg, 0.35 mmol) and acetic anhydride (130 mL, 1.38 mmol) in methanol (10 mL), and the resultant mixture deoxygenated by three vacuum nitrogen purging cycles. The reaction was then stirred at room temperature in the dark for 16.5 h followed by removal of the volatiles in vacuo. The crude material was taken up in the minimum amount of dichloromethane (<10mL) and precipitated into ether (200 mL). The precipitate was isolated by centrifugation (3 min at 3000 rpm) followed by decantation of the supernatant and drying. The precipitate was collected and further purified by column chromatography over silica using methanol/chloroform (1:9) as eluent followed by removal of the solvents and recrystallization from an ethanol/petroleum mixture to give 1 as a green crystalline solid (77 mg, 41%),which had an identical 1H NMR spectrum and ES-MS as the literature [35].

Reference： [1]Jansen-Van Vuuren; Deakin; Olsen; Burn [Dyes and Pigments, 2014, vol. 101, p. 1 - 8]

40
[ 5418-63-3 ]
[ 1497-49-0 ]
[ 64-19-7 ]
[ 24136-79-6 ]

Yield	Reaction Conditions	Operation in experiment
54%	at 100℃; for 1h;	1,2,3,3-tetramethyl-3H-indoliumiodide (6.626 g, 22 mmol, 1 eq) and GDH (6.265 g, 22 mmol, 1 eq, TCI) were dissolved in 16 mL of anhydrous acetic acid and the resulting solution was allowed to react at 100 C. for one hour. The reaction mixture was allowed to cool to ambient temperature, a solid was precipitated through addition of distilled water and was purified, and the residue was washed several times with distilled water and dried under reduced pressure (5.88 g, 54%). Rf=0.7 (normal phase, methylene chloride/methanol 5:1 v/v). 1H NMR (400 MHz, CDCl3): delta 8.19-8.15 (d, J=13.7 Hz, 1H), 7.84-6.89 (m, 13H), 5.45-5.39 (dt, J=13.4 Hz, 11.7 Hz, 1H), 4.2 (s, 3H), 1.92 (s, 3H), 1.72 (s, 6H), 1.64 (s, 3H).

Reference： [1]Patent: US8729276,2014,B2 .Location in patent: Page/Page column 46; 47

41
[ 5418-63-3 ]
phenyl[3-phenylaminoprop-2-en-1-ylidene]ammonium chloride [ No CAS ]
[ 36536-22-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium acetate In acetic anhydride at 80℃; for 0.333333h; Microwave irradiation; Green chemistry;	4.13. General microwave assisted synthesis for NIR dyes General procedure: A mixture of indolium salt (40 mg, 0.154 mmol), bis-iminium salt (20 mg, 0.077 mmol), NaOAc (17 mg, 0.23 mmol) and acetic anhydride (1 mL) was placed in sealed microwave vessel with stirring bar. Sealed vessel was placed in single-mode microwave (CEM Discover) on standard power setting, at indicated temperature,see Table 1 for 20 min resulting in increased pressure (40-100 psi). Reaction mixture was diluted with diethyl ether (10-20 mL) and filtered in vacuo. Solid was washed twice with diethyl ether (5 mL). A clean filter flask was attached to the funnel and the resulting solid was dissolved with dichloromethane (10-15 mL) leaving unreacted sodium acetate crystals on the filter funnel. The filtrate was transferred to a clean round bottom flask and dichloromethane was removed with a rotary evaporator. Metallic blue/green crystals were formed after solvent removal resulting in the yield of individual compounds reported in Table 2. Compounds 17-21, 23 and 24 have been previously reported by conventional method [16].
98%	With sodium acetate; acetic anhydride In neat (no solvent) for 0.333333h; Microwave irradiation; Inert atmosphere; Green chemistry;	4.13 General microwave assisted synthesis for NIR dyes General procedure: A mixture of indolium salt (40mg, 0.154 mmol), bis-iminium salt (20 mg, 0.077 mmol), NaOAc (17 mg, 0.23 mmol) and acetic anhydride (1 mL) was placed in sealed microwave vessel with stirring bar. Sealed vessel was placed in single-mode microwave (CEM Discover) on standard power setting, at indicated temperature, see Table 1 for 20 min resulting in increased pressure (40-100 psi). Reaction mixture was diluted with diethyl ether (10-20 mL) and filtered in vacuo. Solid was washed twice with diethyl ether (5mL). A clean filter flask was attached to the funnel and the resulting solid was dissolved with dichloromethane (10-15mL) leaving unreacted sodium acetate crystals on the filter funnel. The filtrate was transferred to a clean round bottom flask and dichloromethane was removed with a rotary evaporator. Metallic blue/green crystals were formed after solvent removal resulting in the yield of individual compounds reported in Table2. Compounds 17-21, 23 and 24 have been previously reported by conventional method [16].

Reference： [1]Owens, Eric A.; Bruschi, Nicholas; Tawney, Joseph G.; Henary, Maged [Dyes and Pigments, 2015, vol. 113, p. 27 - 37]
[2]Owens, Eric A.; Bruschi, Nicholas; Tawney, Joseph G.; Henary, Maged [Dyes and Pigments, 2015, vol. 113, p. 27 - 37]

42
[ 33985-71-6 ]
[ 5418-63-3 ]
C₂₅H₂₉N₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With acetic anhydride; for 0.0833333h;Reflux;	1,2,3,3-Tetramethyl indolenium iodide (0.24 g, 0.8mmol) and 9-julolidine carboxaldehyde (0.16 g, 0.8 mmol) were refluxed in acetic anhydride (10 mL) for 5 min. The resulting violet precipitate was filtered and dried. Yield: 30%. 1H NMR (500 MHz, DMSO) delta 1.7 (s, 2x3H), 1.9 (t,2x2H), 2.7 (t, 2x2H), 3.4 (t, 2x2H), 3.8 (s, 3H, N-CH3'-H,7.0-8.15 (m, 8x1H, Ar'-H, -CH=CH-).

Reference： [1]Bulletin of the Korean Chemical Society,2014,vol. 35,p. 2453 - 2459

43
3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde [ No CAS ]
[ 5418-63-3 ]
C₂₆H₂₂N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In ethanol for 5h; Reflux;
22%	With piperidine In ethanol at 80℃; for 12h; Inert atmosphere;	Synthesis of HBT-pH2 1 mmol HBT-CHO was dissolvedin 50 mL absolute ethanol. 2 mmol 1,2,3,3-tetramethyl-3H-indole-pyridine iodideand 20 mu L piperidine were added. The mixture was stirred at 80 for 12 h under theprotection of argon gas. After cooling, a large amount of red precipitation wasobtained. After precipitation and filtration, solid phase was collected andrecrystallized in absolute ethanol. The orange target compound HBT-pH2 was obtained with a yield of22%. 1H-NMR (300 MHz, CDCl3, TMS) δH[ppm]:14.07 (s,1H), 8.86 (d, J = 16.5 Hz, 1H), 8.78(d, J = 7.8 Hz, 1H), 8.15 (s, 1H),8.12-7.94 (m, 4H), 7.69-7.58 (m, 6H), 7.52 (d, J = 6.9 Hz, 1H), 4.54 (s, 3H), 1.94 (s, 7H). MS(ESI+): calcd.for C26H22N2OS[M+H+]+411.15, found:411.14.

Reference： [1]Mahapatra, Ajit Kumar; Maiti, Kalipada; Manna, Saikat Kumar; Maji, Rajkishor; Mukhopadhyay, Chitrangada Das; Pakhira, Bholanath; Sarkar, Sabyasachi [Chemistry - An Asian Journal, 2014, vol. 9, # 12, p. 3623 - 3632]
[2]Zhu, Jieji; Gao, Qi; Tong, Qingxiao; Wu, Guangfu [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 225]

44
1-butyl-2-(methylthio)benzo[c,d]indol-1-ium iodide [ No CAS ]
[ 5418-63-3 ]
1-butyl-2-[(1,1,3-trimethyl-1,3-dihydro-1H-indol-2-ylidene)methyl]benzo[c,d]indolium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With triethylamine In acetonitrile at 60℃; for 1h;	General Synthesis of the Monomethine Dyes General procedure: Thioether 4 and each quaternary ammonium salt 5a-d and 9a-c, respectively, were dissolved inacetonitrile and a catalytic amount of triethlyamine was added to the solution. The reaction mixturewas refluxed at 60 C for 1 h and monitored by UV-Vis. Upon cooling to room temperature, thecorresponding dyes 6a-d and 10a-c were precipitated by adding diethyl ether. The solid was collectedby vacuum filtration and triethylammonium salts were removed by washing with deionized water.The final dyes were purified via precipitation from methanol with diethyl ether.

Reference： [1]Soriano, Eduardo; Holder, Cory; Levitz, Andrew; Henary, Maged [Molecules, 2016, vol. 21, # 1]

45
C₁₆H₁₃NO₄ [ No CAS ]
[ 5418-63-3 ]
C₂₈H₂₇N₂O₃⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With piperidine In ethanol for 10h; Reflux;	1 Example 1 N-n-propyl-3-formyl-4-hydroxy-1,8-naphthalenedicarboxylic anhydride 0.566g (2mmol) and 1,2,3,3-tetramethyl-3H-indolium iodide 0.662g (2.2mmol) was dissolved in 20 ml ethanol. Under 100 μL piperidine catalysis, reflux for 10 hours, and after cooling, the filter cake is washed with ethanol washing (5 ml * 3), vacuum drying to obtain red-brown solid, PPEI the target compound, 1.030g, yield 91.0%.

Reference： [1]Current Patent Assignee: Shanxi University; Yin, Caixia; Li, Jianfang; Liu, Tao; Huo, Fangjun - 2016 Location in patent: Paragraph 0026; 0031; 0032

46
[ 53566-95-3 ]
[ 5418-63-3 ]
2,2’-((1E,1’E)-((phenylazanediyl)bis(4,1-phenylene))bis(ethene-2,1-diyl))bis(1,3,3-trimethyl-3H-indol-1-ium)iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With piperidine In ethanol for 10h; Reflux;	1 example 1 N, N-bis (4-formyl-phenyl) aniline 0.603g (2mmol) and 1, 2, 3, 3-tetramethyl -3H-indole iodide 1.325g (4.4mmol) is completely dissolved in 20 ml ethanol, adding 50 μ L piperidine catalytic, reflux 10 hours, after the completion of reaction the reaction solution is concentrated by distillation under reduced pressure, and after cooling to obtain brown solid 1.561g, yield 90.0%, is triphenylamine Diindole Iodized salt.

Reference： [1]Current Patent Assignee: SHANXI UNIVERSITY - CN105777607, 2016, A Location in patent: Paragraph 0026

47
[ 5418-63-3 ]
[ 197638-83-8 ]
C₂₈H₃₆N₃O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 10289 - 10292

48
[ 3484-22-8 ]
[ 61010-04-6 ]
[ 5418-63-3 ]
C₃₁H₃₂ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31.5%	In ethanol; for 2.0h;Inert atmosphere; Reflux;	The mixture of compound 2 (6.02 g, 20 mmol),compound 3 (4.08 g, 20 mmol), compound 4 (3.45 g, 20 mmol) and 50 mL ethanolwas stirred under reflux for 2 h under N2 atmosphere. After cooling to roomtemperature, it was concentrated to afford a dark blue solid, which was purified byflash chromatography (petroleum ether/dichloromethane/ethyl acetate = 8:4:1, V/V/V)to yield a blue solid (3.24 g, 31.5%). 1H NMR (400 MHz, CDCl3) delta (ppm): 8.27 (2H,dd, J1 = 16.6Hz, J2 = 9.2 Hz), 8.16 (1H, d, J = 2.1 Hz), 7.64 - 7.60 (2H, m), 7.19 (2H,t, J = 8.1 Hz), 6.91 (1H, t, J = 7.4 Hz), 6.68 (1H, d, J = 7.8 Hz), 6.58 (1H, d, J = 16.0 Hz), 5.46 (1H, d, J = 12.7 Hz), 3.21 (3H, s), 2.60 (4H, dd, J1 = 11.2 Hz, J2 = 5.4 Hz),1.96 - 1.85 (2H, m), 1.66 (6H, s), 1.52 (6H, s). 13C NMR (100 MHz, CDCl3) delta (ppm):189.10, 160.91, 159.96, 147.74, 145.10, 144.70, 139.87, 139.73, 139.19, 128.72,127.86, 127.82, 124.81, 121.72, 120.42, 120.03, 118.12, 116.90, 106.42, 93.31, 52.97,46.16, 29.30, 28.22, 26.88, 26.35, 24.39, 21.38. HRMS (ESI Positive): calc. forC31H32ClN3O2, [M+H]+ (m/z) 514.2256, found 514.2257.

Reference： [1]Chinese Chemical Letters,2017,vol. 28,p. 1681 - 1687

49
N-((E)-(2-phenyl-3-((E)-(phenylimino)methyl)cyclohex-2-enylidene)methyl)aniline hydrochloride [ No CAS ]
[ 5418-63-3 ]
1,3,3-trimethyl-2-((E)-2-((E)-6-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)-3,4,5,6-tetrahydro-[1,1'-biphenyl]-2-yl)vinyl)-3H-indol-1-ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium acetate; acetic anhydride at 60℃;	General procedure: The various salts 3 (2 molar eq), the dianil linker 5 (1 molar eq), and sodium acetate (2 molareq) were dissolved in acetic anhydride and heated to 60 °C for 2-3 h. The crude product was thenprecipitated with diethyl ether, collected, and washed with methanol to yield heptamethine dyes 6 aspure sample.

Reference： [1]Levitz, Andrew; Marmarchi, Fahad; Henary, Maged [Molecules, 2018, vol. 23, # 2]

50
[ 5418-63-3 ]
[ 90-02-8 ]
[ 1485-92-3 ]

Yield	Reaction Conditions	Operation in experiment
81%	With cholin hydroxide In water at 80℃; for 1h;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).Characterization data for selected spiropyran(SP-1): 10,30,30-trimethylspiro[chromene-2,20-indoline]81%; Colorless solid; M.P. 91-92 °C. Reported M.P. 92-94 °C.[25]1H NMR (200 MHz) δ 7.23 (1H, d, J 8.0 Hz, C5-H), 7.06-6.96 (5H, m, C4-H, C8-H,C60-H, C40-H & C7-H), 6.83-6.70 (2H, m, C50-H & C6-H), 6.61 (1H, d, J 8.0 Hz,C70-H), 5.69 (1H, d, J 10.0 Hz, C3-H), 2.57 (3H, s, N-CH3), 1.32 (3H, s, C30-CH3),1.10 (3H, s, C30-CH3). 13C NMR: δ 154.64 (C8-C-O), 148.43 (C70-C-N), 136.28 (C30-CC40),129.57 (C5), 129.40 (C7), 127.37 (C3 & C40), 126.65 (C60), 120.55 (C4-C-C5),119.88 (C4), 119.55 (C6), 118.22 (C50), 114.79 (C8), 106.85 (C70), 105.18 (C2), 51.61(C30), 29.66 (N-CH3), 25.69 (C30-CH3), 20.17 (C30-CH3).LC-MS (m/z): Calculated for C19H20NO (MH) 278.2, Observed 278.2

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

51
[ 5418-63-3 ]
[ 708-06-5 ]
[ 1592-43-4 ]

Yield	Reaction Conditions	Operation in experiment
83%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

52
[ 672-13-9 ]
[ 5418-63-3 ]
[ 20200-73-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With cholin hydroxide; In water; at 80.0℃; for 1.0h;Green chemistry;	General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Synthetic Communications,2018,vol. 48,p. 208 - 215

53
[ 82304-99-2 ]
[ 5418-63-3 ]
6'-ethoxycarbonyl-1,3,3-trimethylspiro[indoline-2,2'-(2H)-chromene] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

54
[ 584-87-2 ]
[ 5418-63-3 ]
[ 23022-08-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	With cholin hydroxide; In water; at 80℃; for 1h;Green chemistry;	General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Synthetic Communications,2018,vol. 48,p. 208 - 215

55
[ 24589-99-9 ]
[ 5418-63-3 ]
[ 20200-71-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

56
[ 673-22-3 ]
[ 5418-63-3 ]
[ 17487-75-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

57
[ 5418-63-3 ]
[ 635-93-8 ]
[ 61431-10-5 ]

Yield	Reaction Conditions	Operation in experiment
88%	With cholin hydroxide In water at 80℃; for 1h; Green chemistry;	General experimental procedure for the synthesis of spiropyrans General procedure: In a general procedure, a mixture of indolium iodide 1 (1.0 mmol), 2-hydroxy arylaldehyde 2 (1.0 mmol) and aqueous solution of 40 wt% choline hydroxide (1.5 mmol)was stirred at 80 °C for 1 h. Then reaction mixture was cooled to room temperature, the solid product was filtered off and washed with water. The crude product was purified by column chromatography on silica gel with hexane:ethyl acetate (95:05) as the eluent toafford the corresponding spiropyran 3 (Scheme 3).

Reference： [1]Pargaonkar, Jyotsna G.; Patil, Sanjay K.; Vajekar, Shailesh N. [Synthetic Communications, 2018, vol. 48, # 2, p. 208 - 215]

58
(E)-2-((2-butoxy-3,4-dioxocyclobut-1-en-1-yl)methylene)-1,3,3-trimethyl-indoline-5-carboxylic acid [ No CAS ]
[ 5418-63-3 ]
C₂₉H₂₈N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine In toluene; butan-1-ol for 24h; Dean-Stark; Reflux; Inert atmosphere;	5 Example 5: Synthesis of unsymmetrical SQ compounds: General procedure: Indolium iodide derivatives (5a, 6a, 6b, 7a, 7b; 1 equiv.) and semi-squaraine derivatives (8, 9, 10, 11; 1 equiv.) were dissolved in 1-butanol and dry toluene (1: 1, 3 niL each)in a 50 niL two necked round bottomed flask, dry pyridine (1.5 equiv.) was added to it and charged with Dean-Stark apparatus according the Scheme 2. The reaction mixture was refluxed for 24h under inert atmosphere. The reaction mixture was cooled to room temperature and the solvents were removed under reduced pressure. The reaction mixture was subjected to column chromatography (Si02, 100-200 mesh, 5% CH3OH and 95% CH2C12) to afford the required dye as green coloured solids. In case of 18, pet.ether and EtOAc were used as eluents. (0121) 5-Carboxy-2-[[3-[(l,3-dihydro-l,3,3-trimethyl-2H-indol-2-ylidene)methyl]-2-hydroxy- 4- oxo-2-cyclobuten-l-ylidene]methyl]-l,3,3-trimethyl-3H-indolium (SQ-1): 0.17 g, Yield: 87%; 1H NMR (CDC13, 200MHz) δ: 8.11 (dd, 7=8.1, 1.4 Ηζ,ΙΗ), 8.03 (s, 1H), 7.47-7.32 (m, 3H), 7.09 (d, 7=7.6Hz, 1H), 6.98 (d, 7=8.6 Hz, 1H), 6.09 (s, 1H), 5.99 (s, 1H), 3.67 (s, 3H), 3.53 (s, 3H), 1.80 (b, 12H); 13C NMR (CDC13,100 MHz) δ: 181.4, 176.6, 172.8, 169.4, 168.8, 146.8, 145.1,142.2, 141.6, 141.3, 130.7, 128.2, 127.6, 124.4, 123.4, 121.9, 109.6, 107.9, 87.6, 87.3, 61.5, 49.4, 47.9, 33.3, 31.1, 30.2, 26.8, 26.3;HRMS (m/z):[M+H]+calcd for C29H29N204: 469.2128; found: 469.2118.

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2018/20518, 2018, A1 Location in patent: Page/Page column 25

59
[ 102275-67-2 ]
[ 5418-63-3 ]
C₂₅H₂₄NO₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	In ethanol for 16h; Reflux; Inert atmosphere;
94%	In ethanol at 80℃; for 16h; Inert atmosphere;	1.2 (2) Compound 2 (214.2 mg, 1.0 mmol) and 1,2,3,3-tetramethyl-3H-indole iodide (301.2 mg, 1.0 mmol) were mixed with ethanol.The condensation reaction was carried out at 80 ° C under nitrogen for 16 h;After the obtained condensed material was cooled, diethyl ether (30 mL) was added to recrystallize to give a red solid.The calculated yield was 94%;

Reference： [1]Wang, Jianguo; Chen, Qingqing; Tian, Na; Zhu, Wenping; Zou, Hang; Wang, Xuesong; Li, Xiaokang; Fan, Xiaolin; Jiang, Guoyu; Tang, Ben Zhong [Journal of Materials Chemistry B, 2018, vol. 6, # 11, p. 1595 - 1599]
[2]Current Patent Assignee: GANNAN NORMAL UNIVSERTIY - CN108164450, 2018, A Location in patent: Paragraph 0060; 0062; 0068; 0069

60
[ 5418-63-3 ]
((E)-2-chloro-3-(hydroxymethylene)cyclohexene-1-ene-1-carbaldehyde) [ No CAS ]
2‐(2‐{2‐chloro‐3‐[2‐(1,3,3‐trimethylindol‐2‐ylidene)ethylidene]cyclohex‐1‐en‐1‐yl}ethenyl)‐1,3,3‐trimethylindol‐1‐ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With sodium acetate; acetic anhydride; acetic acid at 120℃; for 4h;	2.2.3. Synthesis of 2-(2-[2-chloro-3-([1,3-dihydro-1,3,3-trimethyl-2Hindol-2-ylidene]ethylidene)-1-cyclohexen-1-yl]ethenyl)-1,3,3-trimethylindolium iodide (4) 1,2,3,3-Tetramethyl-3H-indolium iodide (3) (2.5 g, 8.31 mmol),dialdehyde 2 (0.478 g, 2.77 mmol) and CH3COONa (1.36 g, 16.62mmol) were added to a mixture of acetic acid and acetic anhydride (1:1,108 mL) and the mixture was heated for 4 h at 120 °C. Subsequently, thesolvent was evaporated and the residue was partitioned between CH2Cl2(50.0 mL) and water (30 mL) and the organic layer was dried over sodiumsulphate and the solvent was evaporated in vacuo. The crudeproduct was purified by flash column chromatography to yield compound4 as a green solid (2.84 g, 74%), [eluting solvent system: CH2Cl2/CH3OH, (98:2 to 95:5)]. 1H NMR (300 MHz, DMSO-d6) δ: 1.67 (s, 12H),1.92-1.79 (dt, J = 11.8, 6.3 Hz, 2H), 2.71 (t, J = 6.0 Hz, 4H), 3.68 (s,6H), 6.30 (d, J = 14.2 Hz, 2H), 7.25-7.33 (m, 2H), 7.44 (d, J = 4.1 Hz,4H), 7.62 (d, J = 7.3 Hz, 2H), 8.25 (d, J = 14.2 Hz, 2H). 13C NMR (600MHz, DMSO-d6) δ: 20.4, 25.9, 27.3, 31.6, 48.8, 101.8, 111.4, 122.3,125.1, 126.0, 128.5, 140.9, 142.6, 142.8, 147.6, 172.6.
2.7 g	In toluene; butan-1-ol for 4h; Inert atmosphere; Reflux;	Synthesis of IR-786 iodide 4 (E)-2-chloro-3-(hydroxymethylene)cyclohex-1-ene-1-carbaldehyde 3 (1 g, 5.8 mmol) and N-methyl-2,3,3-trimethylindolinium iodide 2 (3.5 g, 11.6 mmol) were taken up in n-butanol:toluene (7:3, 20 mL) in a 250 mL round bottom flask. The reaction mixture was heated to reflux for 4 h. The colour of the reaction mixtures changes from brown to dark green. The solvent was evaporated under reduced pressure and dried under vacuum for 1 h. The solids obtained were taken up in MeOH (60 mL) and filtered to obtain product as green solid (2.7 g, 71 %). The dye was stored at -5 oC in the dark. Rf = 0.3 (silica gel, 5% MeOH in DCM) 1H NMR (400 MHz, CDCl3): 8.34 (d, 2H, J = 14.17 Hz), 7.43 - 7.37 (m, 4 H), 7.25 - 7.23 (m, 2H), 7.18 (d, 2H, J = 7.92 Hz), 6.25 (d, 2H, J = 14.12 Hz), 3.77 (s, 6H), 2.77 (t, 4H, J = 6.12 Hz), 2.02 - 1.95 (m, 2H), 1.73 (s, 12H); 13C NMR (CDCl3, 400 MHz) δ 173.0 (2C), 150.7, 144.4 (2C), 143.0 (2C), 141.3 (2C), 129.0 (2C), 128.2 (2C), 125.5 (2C), 122.3 (2C), 111.0 (2C), 102.1 (2C), 49.4 (2C), 32.9 (2C), 28.3 (4C), 27.1 (2C), 20.9. LCMS (ESI positive) m/z 484.3 (M + H)+ HRMS (m/z): calculated for C32H36ClN2+: 483.2562; found: 483.25902.
	With acetic anhydride

Reference： [1]Prousis, Kyriakos C.; Canton-Vitoria, Ruben; Pagona, Georgia; Goulielmaki, Maria; Zoumpourlis, Vassilis; Tagmatarchis, Nikos; Calogeropoulou, Theodora [Dyes and Pigments, 2020, vol. 175]
[2]Choi, Peter; Noguchi, Katsuya; Ishiyama, Munetaka; Denny, William A.; Jose, Jiney [Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2013 - 2017]
[3]Wang, Kaiping; Nie, Gang; Ran, Siqi; Wang, Huiling; Liu, Xiqiu; Zheng, Ziming; Zhang, Yu [Dyes and Pigments, 2020, vol. 172]

61
[ 698-27-1 ]
[ 5418-63-3 ]
1'-ethyl-3',3',7-trimethylspiro[chromene-2,2'-indoline] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With piperidine In ethanol for 12h; Reflux;	2.3 Preparation and Characterization of Compound A-F General procedure: 1,2,3,3-tetramethyl-3H-indolium iodide (1.88g, 10mmol), 4-substituted 2-hydroxy-benzaldehyde (10mmol) and 2.0mL piperidine were dissolved in 25mL of CH3CH2OH, and the reaction mixture was refluxed with stirring for 12h and then the solvents were evaporated in reduced pressure. The residue was purified by column chromatography on silica gel to give target compounds. Yield: 45-59%. The structure of A-F fully characterized by 1H NMR, 13C NMR and HRMS-ESI. (see the Fig. S4-Fig. S21).

Reference： [1]Cui, Lixia; Zhang, Honghong; Zhang, Guomei; Zhou, Ying; Fan, Li; Shi, Lihong; Zhang, Caihong; Shuang, Shaomin; Dong, Chuan [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2018, vol. 202, p. 13 - 17]

62
C₁₃H₉NO₃ [ No CAS ]
[ 5418-63-3 ]
C₂₅H₂₃N₂O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%	With sodium acetate In acetic anhydride at 80℃; for 6h; Inert atmosphere;	1.2 (2) Synthesis of structural formula 2-(4-Pyridinic acid ester styryl)-1,3,3-trimethyl-3H-indole iodide salt represented by Formula (1): The specific process is:The 4-picolinic acid benzaldehyde (340 mg, 1.5 mmol) obtained in step (1)1,2,3,3-Tetramethyl-3H-indole iodide salt (301 mg, 1 mmol) and anhydrous sodium acetate (123 mg, 1.5 mmol)Soluble in anhydrous acetic anhydride (2mL)The reaction was heated to 80°C for 6 hours under argon protection.After the reaction is complete,Cool to room temperatureQuench with water (8 mL),There is a solid precipitated,Filter and wash with ethyl acetate,The collected solids are copper ion fluorescent probes.That is, the compound represented by the formula (1)The yield is 35%.

Reference： [1]Current Patent Assignee: UNIV HEZHOU - CN107629036, 2018, A Location in patent: Paragraph 0054; 0055; 0056; 0057; 0058; 0059; 0060

63
C₂₉H₃₀N₄O₄ [ No CAS ]
[ 5418-63-3 ]
C₄₁H₄₄N₅O₃⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With trifluoroacetic acid In ethanol at 80℃; for 8h;	1.3 (3) 4-Piperazinyl-(4-benzaldehyde)-N-(2-morpholinoethyl)naphthalimide (compound 3, 498 mg, 1 mmol), trifluoroacetic acid (20 μL, CAS: 76-05-1) And 1,2,3,3-tetramethyl-3H-indolium iodide (301 mg, 1 mmol, CAS: 5418-63-3) was added to the ethanol solution and heated to 80 °C for 8 h, then the solvent was swirled. Dry, using a column chromatography to give the reddish brown compound as the probe Na-SO2 (331 mg, yield 51%), and the H NMR spectrum is shown in Fig. 1.

Reference： [1]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN108129459, 2018, A Location in patent: Paragraph 0039

64
C₂₇H₂₇NO₃ [ No CAS ]
[ 5418-63-3 ]
C₃₉H₄₁N₂O₂⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With piperidine In ethanol at 70℃; for 4h; Inert atmosphere;	2.2.2 Synthesis of L Compound 3 (250mg, 0.6mmol), 1,2,3,3-tetramethyl-3H-indolium iodide (192mg, 0.63mmol) were taken in a 100ml round-bottomed flask. 10ml of dry ethanol was added to the mixture under N2 atmosphere. Then 10μL of piperidine was added to it. The whole suspension was heated at 70°C for 4h. The suspension became solubilised under heating condition. Upon slow cooling L got precipitated from the solution. The solid was filtered, washed with cold ethanol and dried in vacuum to get the pure compound. Yield: 230mg (55%). ESI-MS: m/z calculated for [L-I]+ 569.3163 found 569.4860 (Fig. S6); Elemental analysis for C39H41IN2O2: found: C, 67.24; H, 5.93; N, 4.02. Calculated: C, 67.37; H, 5.98; N, 4.15; 1H NMR (300MHz, ACN-d3): δ (ppm)=0.88 (t, 3H, J=7.5Hz), 1.30-1.39 (m, 10H), 1.72 (m, 2H), 1.85 (s, 6H), 4.11-4.15 (m, 5H), 7.58 (d, 1H, J=15Hz), 7.65-7.84 (m, 8H, Ar-H), 8.21 (d, 2H, J=9Hz, Ar-H), 8.29 (d, 1H J=9Hz, Ar-H), 8.38 (d, 1H, J=15Hz), 8.59-8.63 (m, 2H, Ar-H) (Fig. S4); 13C NMR (75MHz, ACN-d3): δ (ppm)=13.3, 22.3, 24.9, 26.8, 27.7, 28.9, 29.0, 31.5, 34.8, 40.1, 52.8, 113.5, 115.1, 122.6, 122.8, 123.2, 127.5, 128.1, 128.5, 129.3, 129.5, 130.1, 130.1, 130.3, 130.8, 131.0, 131.9, 134.2, 141.8, 143.6, 144.9, 152.6, 163.7, 163.9, 182.6 (Fig. S5).

Reference： [1]Maji, Siddhartha; Chowdhury, Bijit; Pal, Sanchari; Ghosh, Pradyut [Inorganica Chimica Acta, 2018, vol. 483, p. 321 - 328]

65
[ 25016-02-8 ]
[ 5418-63-3 ]
(E)-1,3,3-trimethyl-2-(2-methoxy-5-nitrostyryl)-3H-indol-1-ium iodide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 4825 - 4834

66
[ 5418-63-3 ]
[ 63857-00-1 ]
2-((E)-2-((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindolin-2-ylidene)ethylidene)cyclohex-1-en-1-yl)vinyl)-1,3,3-trimethyl-3H-indol-1-ium iodide [ No CAS ]

Reference： [1]Photochemical and Photobiological Sciences,2018,vol. 17,p. 1409 - 1416

67
[ 5418-63-3 ]
[ 131-91-9 ]
[ 27333-47-7 ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: A mixture of indolium iodide 1 (1.0 mmol) and choline hydroxide (10 mol %) in water (3 mL) was stirred at 80 C for 20 min. Then 1-nitroso-2-naphthol 2 (1.0 mmol) was added and the resulting mixture stirred at 80C for another 40 min. Then reaction mass was cooled to rt. The solid product was then filtered and washed with water. The synthesized product was finally purified using column chromatography technique (silica gel 100-200 mesh size) with ethyl acetate:hexane (05:95) as an eluent to give the desired spironaphthoxazine (Scheme 2 & Table 1). SNO-1: 1,1,3-trimethyl-1,3-dihydrospiro[benzo[e]indole-2,3'-naphtho[2,1-b][1,4]oxazine] Yield: 89%; Colorless solid; mp 123-124 oC. Reported mp 125. A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2- naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to further spiroheterocyclic oxazines are possible. 1H NMR (500 MHz, DMSO-d6) delta 8.499 (1H, d, J = 8.5 Hz, C10?-H), 7.968 (1H, s, C2?-H), 7.912 (1H, d, J = 8.6 Hz, C7?-H), 7.870-7.825 (3H, m, C6?-H, C8?-H, & C9?-H), 7.590 (1H, t, J = 8.3 Hz, C6-H), 7.418 (2H, m, C4 & C5?-H), 7.243 (1H, t, J = 8.0 Hz, C5-H), 7.075 (1H, d, J = 8.5 Hz, C7-H), 2.778 (3H, s, N-CH3), 1.594 (3H, s, C1-CH3), 1.472 (3H, s, C1-CH3).
60%	In isopropyl alcohol; at 20℃;Inert atmosphere;	General procedure: To1,3,3-trimethyl-2-methylenedihydroindole(I5) (1 equivalent)Isopropanol(15 V, relative to hydrazine) was added nitroso naphthol (1 equivalent) to the solution.Then, under nitrogen, the mixture was stirred at reflux overnight, and cooled to room temperature.Spin dry. The residue was purified by column (eluent was petroleum ether / ethyl acetate).The desired product is obtained.

Reference： [1]Synthetic Communications,2020,vol. 50,p. 338 - 347
[2]Patent: CN109206440,2019,A .Location in patent: Paragraph 0058; 0060; 0061; 0063

68
[ 1201-91-8 ]
[ 5418-63-3 ]
E-2-(4-((2-hydroxyethyl)(methyl)amino)styryl)-1,3,3-trimethyl-3H-indol-1-ium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With piperidine In ethanol at 80℃;

Reference： [1]Chung, Andrew J.; Deore, Prashant S.; Al-Abdul-Wahid, Sameer; Aboelnga, Mohamed M.; Wetmore, Stacey D.; Manderville, Richard A. [Journal of Organic Chemistry, 2019]

69
C₁₁H₁₀O₃ [ No CAS ]
[ 5418-63-3 ]
C₃₅H₃₈N₂O⁽²⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium acetate In acetic anhydride at 80℃; for 0.5h;	A mixture of CO-A (65 mg, 0.33 mmol), NaOAc (83.9 mg,1.02 mmol), and commercially available 1, 2, 3, 3-tetramethyl-3H-indoliumiodide (210.6 mg, 0.70 mmol) was dissolved in 2 mL Ac2O. Thereaction mixture stirred for 30 min at 80 °C under an Ar atmosphere.After completion, the solvent was evaporated under reduced pressure,and the crude product was dissolved in MeCN, filtered and concentratedto give CO-B as a red solid (144 m, yield 54%). 1H NMR(500 MHz, CDCl3) δ 9.80 (s, 1H), 9.07 (d, J=8.5 Hz, 1H), 8.85 (d,J=16.1 Hz, 1H), 8.71 (d, J=16.4 Hz, 1H), 8.37 (d, J=16.4 Hz, 1H),8.13 (d, J=16.1 Hz, 1H), 7.64-7.49 (m, 8H), 7.28-7.23 (m, 1H),6.18-6.06 (m, 1H), 5.55-5.48 (m, 1H), 5.43 (dt, J=10.6, 5.3 Hz, 1H),4.81 (d, J=5.3 Hz, 2H), 4.58 (s, 3H), 4.52 (s, 3H), 2.01 (s, 6H), 1.85 (t,J=8.7 Hz, 6H). 13C NMR (151 MHz, CDCl3) δ 183.59 (s), 162.49 (s),154.48 (s), 148.40 (s), 143.98 (s), 143.33 (s), 141.45 (s), 139.96 (s),135.32 (s), 131.59 (s), 130.26 (s), 129.92 (s), 129.88 (s), 129.46(s),128.56 (s), 123.49 (s), 122.94 (s), 122.84 (s), 119.48 (s), 114.65 (s),114.34 (s), 114.23 (s), 112.91 (s), 113.98 (s), 70.36 (s), 53.03 (s), 52.52(s), 37.84 (s), 37.62 (s), 27.47 (s), 27.10 (s). The compound was analyzedby HRMS, the peak at m/z 503.2350 [M+H]+.

Reference： [1]Zhang; Wang, Yu; Dong, Junqiang; Zhang, Yonggao; Zhu, Jiawen; Gao, Jianbo [Dyes and Pigments, 2019, vol. 171]

70
[ 5418-63-3 ]
[ 457897-31-3 ]
2,2'-((1E,1'E)-(6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(1,3,3-trimethyl-3H-indol-1-ium) iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.1%	With piperidine In ethanol for 24h; Inert atmosphere; Reflux;	2,2'-((1E,1'E)-(6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(ethene-2,1-diyl))bis(1,1,3-trimethyl-1H-benzo[e]indol-3-ium) iodide (4) Under N2, 278.3 mg (1 mmol) TB2, 1.20 g (4 mmol) 04 and 0.1 mL piperidine were refluxed for 24 h in 10 mL absolute ethyl alcohol. When cooled to room temperature, the mixture was filtered and washed with EtOH. The residue was recrystallized from MeOH and toluene to give 4 (502.6 mg, 85.1 % yield) as red grain.

Reference： [1]Li, Jinyan; Zhuge, Xiangxue; Li, Yexin; Yuan, Chunxue [Tetrahedron, 2019, vol. 75, # 48]

71
[ 5418-63-3 ]
[ 49764-63-8 ]
8,9-dibromo-5,12,12-trimethyl-5,12-dihydroquinolino[2,3-b]quinoxaline [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 13709 - 13713

72
[ 5418-63-3 ]
2,3-dihydroxy-1-nitrosonaphthalene [ No CAS ]
[ 132036-04-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide With cholin hydroxide In water at 80℃; for 0.333333h; Green chemistry; Stage #2: 2,3-dihydroxy-1-nitrosonaphthalene In water at 80℃; for 0.666667h; Green chemistry;	General method for the synthesis of spironaphthoxazines General procedure: A mixture of indolium iodide 1 (1.0 mmol) and choline hydroxide (10 mol %) in water (3 mL) was stirred at 80 °C for 20 min. Then 1-nitroso-2-naphthol 2 (1.0 mmol) was added and the resulting mixture stirred at 80°C for another 40 min. Then reaction mass was cooled to rt. The solid product was then filtered and washed with water. The synthesized product was finally purified using column chromatography technique (silica gel 100-200 mesh size) with ethyl acetate:hexane (05:95) as an eluent to give the desired spironaphthoxazine (Scheme 2 & Table 1).

Reference： [1]Vajekar, Shailesh N.; Shankarling, Ganapati S. [Synthetic Communications, 2020, vol. 50, # 3, p. 338 - 347]

73
[ 65300-88-1 ]
[ 5418-63-3 ]
[ 74388-39-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide With cholin hydroxide In water at 80℃; for 0.333333h; Green chemistry; Stage #2: 1-nitroso-7-methoxy-β-naphthol In water at 80℃; for 0.666667h; Green chemistry;	General method for the synthesis of spironaphthoxazines General procedure: A mixture of indolium iodide 1 (1.0 mmol) and choline hydroxide (10 mol %) in water (3 mL) was stirred at 80 °C for 20 min. Then 1-nitroso-2-naphthol 2 (1.0 mmol) was added and the resulting mixture stirred at 80°C for another 40 min. Then reaction mass was cooled to rt. The solid product was then filtered and washed with water. The synthesized product was finally purified using column chromatography technique (silica gel 100-200 mesh size) with ethyl acetate:hexane (05:95) as an eluent to give the desired spironaphthoxazine (Scheme 2 & Table 1).

Reference： [1]Vajekar, Shailesh N.; Shankarling, Ganapati S. [Synthetic Communications, 2020, vol. 50, # 3, p. 338 - 347]

74
6,6,12,12-tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2',3'-d’]-s-indaceno[1,2-b:5,6-b’]dithiophene-2,8-dicarboxaldehyde [ No CAS ]
[ 5418-63-3 ]
6,6,12,12‑tetrakis(4‑hexylphenyl)‑6,12‑dihydrodithieno[2,3‑d:2',3'‑d']‑s‑indaceno[1,2‑b:5,6‑b']dithiophene‑2,8‑di(2‑vinyl‑1,3,3‑trimethyl‑3H‑indolium iodide) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With piperidine In ethanol for 4h; Inert atmosphere; Reflux;	Synthesis of probe 6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b']dithiophene-2,8-di(2-vinyl-1,3,3-trimethyl-3H-indoliumiodide) IDTTH A mixture of 6,6,12,12-Tetrakis(4-hexylphenyl)-6,12-dihydrodithieno[2,3-d:2',3'-d']-s-indaceno[1,2-b:5,6-b′]dithiophene-2,8-dicarboxaldehyde (0.108 g, 0.1 mmol) and 1,2,3,3-Tetramethyl-3H-indolium iodide (0.075 g, 0.25 mmol) were suspended in 20 mL ethanol with 0.1 mL piperidine. The reaction mixture was refluxed under N2 atmosphere for 4 h, and concentrated by a rotary evaporator to remove the solvents. A dark blue residue was obtained and purified with column chromatography on 200-300 mesh silica using CH2Cl2:Methanol (50:1, 40:1, 30:1) mixture to obtain a dark blue solid (0.1 g, 0.072 mmol) in 72% yield. 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 2H), 8.79 (m, 6H), 7.64 (s, 2H), 7.54-7.53 (m, 4H), 7.51-7.45 (m, 2H), 7.40-7.36 (m, 2H), 7.15 (m, 12H), 6.99-6.95 (m, 2H), 4.20 (s, 6H), 3.16 (m, 8H), 2.64-2.49 (m, 8H), 1.95-1.94 (m, 8H), 1.85 (s, 12H), 1.72-1.52 (m, 16H), 1.43-1.41 (m, 4H), 1.29 (m, 18H). 13C NMR (100.6 MHz, CDCl3) δ 180.13, 155.48, 152.86, 147.47, 147.06, 145.25, 142.59, 142.43, 141.71, 138.81, 136.98, 130.56, 129.51, 128.91, 127.81, 126.11, 122.77, 118.57, 115.93, 113.91, 63.02, 52.12, 44.54, 35.86, 35.61, 33.83, 31.93, 31.69, 31.62, 31.30, 30.29, 29.37, 29.19, 26.96, 22.70, 22.60, 22.15, 22.09, 14.11. HRMS (m/z): calculated for C94H102N2S4Na [M + Na]+, 1409.6813; found: 1409.6818.
70.5%	With piperidine In ethanol at 78℃; for 21h; Inert atmosphere;	1.1 1. Synthesis of a small molecule probe for detecting cyanide ion Take a dry 100mL two-neck bottle, replace the bottle with nitrogen, add6,6,12,12-tetrakis (4-hexylphenyl) -6,12-dihydrodithiophene [2,3-d: 2 ', 3'-d']-s-indeno [1,2-b: 5,6-b '] dithiophene-2,8-dicarbaldehyde(0.108g, 0.1mmol),1,2,3,3-tetramethyl-3H-indolium iodide (0.075g, 0.25mmol),Ethanol (20mL) and a small amount of piperidine (0.15mL), heated at 78 ° C under reflux and stirred for 21h,Subsequently, ethanol and piperidine were removed by distillation under reduced pressure to obtain a dark blue residue.Silica gel column chromatography gradient elution (in order: dichloromethane: methanol = 50: 1,Dichloromethane: methanol = 40: 1, dichloromethane: methanol = 30: 1), separation and purification,A dark blue solid PI (0.1 g, 0.072 mmol) was obtained with a yield of 70.5%.

Reference： [1]Wen, Dan; Deng, Xuankai; Yu, Yanhua [Chemical Papers, 2021, vol. 75, # 3, p. 1095 - 1102]
[2]Current Patent Assignee: JIANGHAN UNIVERSITY - CN110878100, 2020, A Location in patent: Paragraph 0033-0037

75
[ 91958-52-0 ]
[ 5418-63-3 ]
(trans)-2-(4-(bis(2-methoxy-2-oxyethyl)amino)styryl)-1,3,3-trimethyl-3H-indol-1-ium iodide salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With piperidine In ethanol at 20℃; for 5h;	1.2 Step (2): Add 5mmol 1.50g of 1,2,3,3-tetramethyl-indole iodide salt to 30mL absolute ethanol to make it fully dissolved, add the above light yellow oily liquid, add 5mmol, 0.05g Piperidine, react at room temperature for 5 hours, follow the reaction by thin layer chromatography. After the reaction, wash with saturated sodium chloride solution, distill off the organic solvent under reduced pressure, and separate with silica gel column chromatography. The mixed solution with an ester volume ratio of 5: 1 was crystallized to obtain 1.86 g of the target compound as a pale yellow powder with a yield of 68%.

Reference： [1]Current Patent Assignee: GUANGZHOU UNIVERSITY - CN111056985, 2020, A Location in patent: Paragraph 0033; 0034; 0036; 0037

76
[ 5418-63-3 ]
C₁₄H₁₇NO₂ [ No CAS ]
C₂₆H₃₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With triethylamine In methanol at 60 - 64℃; for 9h;	Example 1 Preparation of fluorescent probe QIN-1 General procedure: In a dry 25 mL round-bottom flask, add 0.0717 g (0.33 mmol) 8-hydroxyjulonidine-9-formaldehyde,0.0993 g (0.33 mmol) 1, 2, 3, 3-tetramethyl-3H-indole iodide salt, 30 μL piperidine and 10 mL ethanol. Reflux for 9 h.After cooling, a pink solid was precipitated, suction filtered, the filter cake was washed with ether, and dried to obtain the product. That is the fluorescent probe QIN-1, the yield is 0.0850g, and the yield is 69%.

Reference： [1]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN108047241, 2020, B Location in patent: Paragraph 0031-0033; 0041

77
[ 5418-63-3 ]
C₁₅H₁₉NO₂ [ No CAS ]
C₂₇H₃₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With piperidine In ethanol at 74 - 78℃; for 9h;	Example 1 Preparation of fluorescent probe QIN-1 General procedure: In a dry 25 mL round-bottom flask, add 0.0717 g (0.33 mmol) 8-hydroxyjulonidine-9-formaldehyde,0.0993 g (0.33 mmol) 1, 2, 3, 3-tetramethyl-3H-indole iodide salt, 30 μL piperidine and 10 mL ethanol. Reflux for 9 h.After cooling, a pink solid was precipitated, suction filtered, the filter cake was washed with ether, and dried to obtain the product. That is the fluorescent probe QIN-1, the yield is 0.0850g, and the yield is 69%.

Reference： [1]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN108047241, 2020, B Location in patent: Paragraph 0031-0033; 0041

78
[ 5418-63-3 ]
C₁₆H₂₁NO₂ [ No CAS ]
C₂₈H₃₄N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine In ethanol at 77 - 80℃; for 9h;	Example 1 Preparation of fluorescent probe QIN-1 General procedure: In a dry 25 mL round-bottom flask, add 0.0717 g (0.33 mmol) 8-hydroxyjulonidine-9-formaldehyde,0.0993 g (0.33 mmol) 1, 2, 3, 3-tetramethyl-3H-indole iodide salt, 30 μL piperidine and 10 mL ethanol. Reflux for 9 h.After cooling, a pink solid was precipitated, suction filtered, the filter cake was washed with ether, and dried to obtain the product. That is the fluorescent probe QIN-1, the yield is 0.0850g, and the yield is 69%.

Reference： [1]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN108047241, 2020, B Location in patent: Paragraph 0031-0033; 0041

79
[ 5418-63-3 ]
C₁₇H₂₃NO₂ [ No CAS ]
C₂₉H₃₆N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With piperidine In isopropyl alcohol at 78 - 80℃; for 9h;	Example 1 Preparation of fluorescent probe QIN-1 General procedure: In a dry 25 mL round-bottom flask, add 0.0717 g (0.33 mmol) 8-hydroxyjulonidine-9-formaldehyde,0.0993 g (0.33 mmol) 1, 2, 3, 3-tetramethyl-3H-indole iodide salt, 30 μL piperidine and 10 mL ethanol. Reflux for 9 h.After cooling, a pink solid was precipitated, suction filtered, the filter cake was washed with ether, and dried to obtain the product. That is the fluorescent probe QIN-1, the yield is 0.0850g, and the yield is 69%.

Reference： [1]Current Patent Assignee: NORTHWESTERN UNIVERSITY (ILLINOIS) - CN108047241, 2020, B Location in patent: Paragraph 0031-0033; 0042

80
[ 61010-04-6 ]
[ 5418-63-3 ]
IR-775 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	In toluene; butan-1-ol for 3h; Reflux; Inert atmosphere;	3.1.2. Heptamethine cyanine dye (2) Indolium iodide (0.18 g, 0.6 mmol) and 1 (0.06 g, 0.3 mmol) weredissolved in 20 mL of a mixed solvent of n-butanol and toluene (7:3).The refluxed mixture was reacted for 3 h. followed by cooling to roomtemperature. The solvents were evaporated to yield the yellow-green solid as a crude product. Column chromatography usingmixed solvents(methanol:dichloromethane = 3:97 v/v) was used to purify the crudeproduct. (Rf = 0.27). The bright green product of 2 yield was 0.13 g(99%). 1H NMR (300 MHz, CDCl3): δ 1.73 (s, 12H), 1.90 (m, 2H), 2.75(t, J = 6.0 Hz, 4H), 3.76 (s, 6H), 6.22 (d, J = 15 Hz, 2H), 7.20-7.41(m,8H), 8.35 (d, J = 12 Hz, 2H) ppm.; 13C NMR (75 MHz, CDCl3): δ 20.7(2CH2), 26.8 (CH2), 28.0 (2CH3), 28.1 (2CH3), 32.6 (2CH3), 49.2 (2C),101.7 (2CH), 110.9 (2CH), 122.2 (2CH), 125.4 (2CH), 127.7 (C), 128.8(2CH), 140.1 (2C), 142.8(2C), 144.4 (2CH), 150.6 (2C), 172.9 (2C)ppm; HR-ESI MS cacld for C32H36ClN2+ (M) 483.2562 m/z found483.2562 m/z.
65%	With anhydrous Sodium acetate; acetic anhydride at 120℃; for 2h; Inert atmosphere;	1.3 3) Synthesis of compound 3 Take the compound 1 (2.129g, 7mmol) obtained in step 1), the compound 2 (591mg, 3.5mmol) obtained in step 2) and sodium acetate (1.36g, 10mmol), dissolve them in 20mL of acetic anhydride, under the protection of nitrogen After reacting at 120°C for 2 hours, the precipitate was filtered, washed with petroleum ether and water to obtain a brown precipitate. The crude product was purified by a silica gel column (CH2Cl2: methanol = 30:1) to obtain a dark green solid compound, namely compound 3. The reaction equation is as follows:The yield of compound 3 was 65%;
	In butan-1-ol for 3h; Flash photolysis; Reflux;

In ethanol at 85℃; for 8h;

2-chloro-3-(hydroxymethylene)-1-cyclohexene-1-carboxaldehyde (0.86 g, 5 .00 mmol) and compound M2 (3.01 g, 10.00 mmol) was added into 30 mL ethanol. The mixture was stirred at 85 °C for 8 h. After reaction, the ethanol was evaporated under reduced pressure and the green sand-like solid was obtained. The crude product was purified by silica gel column chromatography to get compound Cy-Cl. Yield: 67.2 %. 1H NMR (600 MHz, CDCl3) δ 8.35 (d, 2H, J = 14.2Hz, =CH2), 7.42-7.37 (m, 4H, Ar-H), 7.26-7.24 (m, 2H, J = 7.5Hz, Ar-H), 7.20 (d, 2H, J = 7.9Hz, Ar-H), 6.25 (d, 2H, J = 14.1Hz, =CH2), 3.76 (s, 6H, -CH3), 2.76 (t, 4H, J = 6.2Hz, -CH2), 1.98 (m, 2H, -CH2), 1.75 (d, 12H, J = 2.1 Hz, 12H, -CH3).

Reference： [1]Chailek, Nirumon; Charoenpanich, Adisri; Hanmeng, Oranual; Phuekvilai, Prattana; Sanmanee, Natdhera; Sirirak, Jitnapa; Swanglap, Pattanawit; Wanichacheva, Nantanit; Yookongkaew, Nimnara [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2020, vol. 240]
[2]Current Patent Assignee: QINGDAO LUOMEISEN OCEAN TECH; INST OCEANOGRAPHIC INSTR SHANDONG ACADEMY OF SCIENCES - CN113461588, 2021, A Location in patent: Paragraph 0059; 0069-0072
[3]Chailek, Nirumon; Kaewnok, Nirawit; Petdum, Anuwut; Sirirak, Jitnapa; Chaneam, Sumonmarn; Kamkaew, Anyanee; Girdthep, Sutinee; Wanichacheva, Nantanit [Journal of Photochemistry and Photobiology A: Chemistry, 2021, vol. 421]
[4]Liu, Jing; Qian, Ying; Shen, Ronghua; Wang, Lingfeng; Zhao, Jie [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 274]

81
[ 5418-63-3 ]
4-(bis(4-(1-ethyl-1H-indol-5-yl)phenyl)amino)benzaldehyde [ No CAS ]
C₅₁H₄₇N₄⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With piperidine In ethanol at 90℃; for 24h; Inert atmosphere;	2.5. Synthesis of TPA 4-(Bis(4-(1-ethyl-1H-indol-5-yl)phenyl)amino)benzaldehyde (100 mg, 0.18 mmol) and 1,2,3,3-tetramethyl-3H-indol-1-ium iodine (64.6 mg, 0.21 mmol) was dissolved in 20 mL ethanol. To the mixture was added piperidine (88 μL, 0.89 mmol) and refluxed at 90 °C in an argon atmosphere for 24 hours. Then the solvent was removed in vacuo. The crude product was purified by silica gel column chromatography with a mixture of dichloromethane:ethyl acetate (80:20) followed by a mixture of dichloromethane:methanol (95:5). TPA was obtained as blue solid (65 mg, 51% yield, mp: >300 oC).

Reference： [1]Dalkilic, Oguzhan; Lafzi, Ferruh; Kilic, Haydar; Saracoglu, Nurullah [Tetrahedron Letters, 2020, vol. 61, # 37]

82
[ 5418-63-3 ]
[ 4185-69-7 ]
[ 19764-96-6 ]

Yield	Reaction Conditions	Operation in experiment
28%	With sodium acetate; aniline In ethanol at 20℃; for 12h;	1,3,3-Trimethyl-2-[(1E,3E,5E)-7-[(2E)-1,3,3-trimethyl-2,3-dihydro-1H-indol-;2-ylidene]hepta-1,3,5-trien-1-yl]-3H-indol-1-ium iodide (5a) To a solution of 4 (0.22 g, 0.80 mmol) in EtOH (10.0 mL) was added 1a (0.60 g, 2.00 mmol). The reaction mixture was stirred for 5 minutes, and then followed by the addition of sodium acetate (0.41 g, 5.00 mmol). The reaction was stirred at room temperature overnight and n-hexane (20.0 mL) was added. The precipitate produced was filtered under suction and washed with n-hexane. The crude product was purified by silica gel column chromatography (solvent; CHCl3:MeOH= 9:1) to obtain cyanine dye 5a (0.12 g, 28%) as a green solid. 1H NMR (d6-DMSO, 400 MHz) δ 7.89 (t, J=13.0 Hz, 2H, CHalkene), 7.79 (t, J=13.0 Hz, 1H, CHalkene), 7.58 (d, J=7.0 Hz, 2H, ArH), 7.41-7.35 (m, 4H, Ar-H), 7.24 (t, J=6.0 Hz, 2H, Ar-H), 6.51 (t, J=13.0 Hz, 2H, CHalkene), 6.32 (d, J=13.0 Hz, 2H, CHalkene), 3.62 (s, 6H, N-CH3), 1.63 (s, 12H, C-CH3). IR (ATR) 2924, 1597, 1438, 1384, 1308, 1141, 987, 887, 740 cm-1. MS (ESI) m/z: 409.21 [M]+. m.p. 178-180 °C, UV abs λmax = 740 nm. [2]

Reference： [1]Critchley, Megan E.; Lawrence, Clare L.; McKenna, Sean T.; Okoh, Adeyi Okoh; Smith, Robert B.; Vishwapathi, Vinod [Bioorganic Chemistry, 2020, vol. 102]

83
[ 5418-63-3 ]
[ 99970-84-0 ]
C₃₆H₃₆N₄⁽²⁺⁾*2I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With pyridine In ethanol at 80℃; for 19h; Inert atmosphere; Darkness;	1 Mixture of 2,2'-bipyridine-4,4'-dicarbaldehyde (0.106g, 0.5mmol) and 1,2,3,3-tetramethyl-3H-indolium iodide (0.301g, 1mmol) Heated to 80 in pyridine/ethanol (16mL; 1:15v/v), reacted for 19 hours under argon atmosphere in the dark, then the reaction was cooled to room temperature, the precipitate was filtered and washed with ether, and the crude product obtained was subjected to ethanol Red-brown crystals were obtained by recrystallization, and the obtained crystals were further dried to obtain 0.241 g of red-brown powder with a yield of 62%.

Reference： [1]Current Patent Assignee: SUN YAT-SEN UNIVERSITY (CHINA) - CN112125887, 2020, A Location in patent: Paragraph 0036-0040

84
[ 3029-19-4 ]
[ 5418-63-3 ]
C₂₉H₂₄N⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.1%	With sodium acetate In ethanol at 85℃; for 16h;	1.2 The synthesis method of compound PH-RISS-1, the specific steps are as follows: (2) In a 10mL round bottom flask, The intermediate compound 1a (0.09g, 0.3mmol) and 1-pyrenecarbaldehyde (0.069g, 0.3mmol) obtained through step (1) were dissolved in 3mL of absolute ethanol, Then add anhydrous sodium acetate (0.024g, 0.03mmol) to the round bottom flask, The reaction mixture was refluxed for 16h at 85°C, A red solid precipitated after cooling to room temperature, Filter to get the red compound, Reuse the dichloromethane/methanol system with a volume ratio of 15:1 to separate and purify the product through the column. To obtain the compound PH-RISS-1, The yield was 90.1%;

Reference： [1]Current Patent Assignee: FUJIAN NORMAL UNIVERSITY - CN112538037, 2021, A Location in patent: Paragraph 0035-0036; 0038; 0040

85
3-(benzo[d]thiazol-2-yl)-2-hydroxybenzaldehyde [ No CAS ]
[ 5418-63-3 ]
C₂₆H₂₃N₂OS⁽¹⁺⁾*I^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With piperidine In ethanol at 80℃; for 2h;	1.2 Add 1mmol of compound 2 (255mg) and 1mmol of hemicyanine derivative (302mg) into a 100mL round-bottomed flask, add 25mL of ethanol to dissolve, add 1 drop of piperidine and stir in an oil bath at 80°C. The reactor was stirred and refluxed for 2 hours, and then the solvent was evaporated under reduced pressure to obtain a solid crude product. The structural formula of the hemicyanine derivative is:(3) The above crude product is purified by silica gel column chromatography (the volume ratio of dichloromethane and methanol in the eluent is 50:1), and 317 mg of fluorescent probe 1 (probe1) can be obtained.Probe 1 (Yield: 59%)
59%	With piperidine In ethanol for 2h; Reflux;	Compound 2 (255 mg, 1 mmol) and hemicyanine derivative(302 mg, 1 mmol) were dissolved in 25 mL EtOH, added 1 mmolpiperidine followly. After reflux stirring for 2 h, the mixture solventwas evaporated and the crude products were purified by columnchromatography to give probe 1 (317 mg, 59 %). 1H NMR(400 MHz, DMSO d6) d = 8.97 (t, J = 7.2, 1H), 8.55 (d, J = 16.3,1H), 8.39 (dd, J = 8.8, 2.0, 1H), 8.16 (d, J = 7.9, 1H), 8.08 (d,J = 8.1, 1H), 7.86-7.79 (m, 1H), 7.56 (dd, J = 14.3, 7.4, 1H), 7.45(d, J = 7.1, 1H), 7.43-7.37 (m, 1H), 7.22 (d, J = 8.8, 1H), 7.16 (d,J = 5.5, 1H), 4.10 (s, 1H), 1.79 (s, 1H).13C NMR (100 MHz, DMSO d6)d181.98, 163.92, 161.90, 153.41, 151.86, 143.95, 142.39, 135.36,134.73, 133.08, 129.47, 129.41, 127.13, 126.95, 126.66, 125.80,123.34, 122.74, 120.25, 118.87, 115.36, 111.14, 52.47, 51.97,34.86, 29.51.ESI-MS m/z [(M -I)+]: 411.1.

Reference： [1]Current Patent Assignee: SHAANXI UNIVERSITY OF CHINESE MEDICINE - CN113004266, 2021, A Location in patent: Paragraph 0039; 0042-0046
[2]Jiang, Bohong; Li, Jiayi; Luo, Weifang; Meng, Qinghua; Tang, Yuping; Ye, Jing; Zhang, Guanghui; Zhang, Shuan [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 267]

86
[ 5418-63-3 ]
4-[(1-methylethyl)amino]-3-nitrobenzaldehyde [ No CAS ]
[ 14075-53-7 ]
C₂₂H₂₆N₃O₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 1,2,3,3-tetramethyl-3H-indolium iodide; 4-[(1-methylethyl)amino]-3-nitrobenzaldehyde With piperidine In ethanol at 90℃; for 24h; Inert atmosphere; Stage #2: potassium tetrafluoroborate In ethanol for 2h; Reflux; Inert atmosphere;	1 Place N-methyl-2,3,3'-trimethylindoline iodide (602mg, 2mmol), Z1 (458mg, 2.2mmol), and piperidine (20μL) in a 50mL round bottom flask, and then add Absolute ethanol (15ml) dissolves all of it. Deoxygenate with nitrogen for 30min, stir at 90°C for 24h, after cooling to room temperature, add KBF4 (504mg, 4mmol) in portions. The reaction solution was refluxed for 2 hours in the dark, cooled and filtered, and the solvent was distilled off under reduced pressure to obtain a crude product. The crude product was recrystallized from acetonitrile to obtain purified orange-pink solid tetrafluoroborate (817 mg) of the cationic group represented by Z2, with a yield of 97%;

Reference： [1]Current Patent Assignee: INST OF ENVIRONMENTAL MEDICINE AND OCCUPATIONAL ME; INST OF ENVIRONMENTAL AND OPERATIONAL MEDICINE ACADEMY OF MILITARY MEDICAL SCIENCE ACADEMY OF MILITA - CN113387865, 2021, A Location in patent: Paragraph 0077; 0085; 0087-0088

87
tetrafluoroboric acid [ No CAS ]
[ 103860-60-2 ]
[ 5418-63-3 ]
C₃₆H₃₆N₂O₂⁽²⁺⁾*2BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: 2,3‐dihydroxynaphthalene‐1,4‐dicarbaldehyde; 1,2,3,3-tetramethyl-3H-indolium iodide With piperidine In ethanol at 95℃; for 24h; Sealed tube; Stage #2: tetrafluoroboric acid In ethanol for 2h; Sealed tube;	2.3. Synthesis of the probe NaIn The compound 2 (50 mg, 0.23 mmol) and 1,2,3,3-tetramethyl-1indolium iodide (152 mg, 0.5 mmol) were dissolved in EtOH(10 mL). Two drops of piperidine were added, the mixture solutionwas stirred for 24 h at 95 C. After cooling, keep stirring for 2 hafter added 150 lL HBF4. In this progress, the product precipitatedas black powder and was isolated by filtration and washing withethanol absolute (136 mg, yield 84%). M.p. 235-237 C; HRMS:m/z [C36H35N2O2-H-2BF4 - ]+ = 527.2698, calcd for 527.2693. 1H NMR(400 MHz, DMSO d6) d = 8.81 (d, J = 16.0 Hz, 2H), 8.34-8.30 (m,4H), 8.00-7.91 (m, 4H), 7.67-7.62 (m, 6H), 4.08 (s, 6H), 1.88 (s,12H). 13C NMR(100 MHz, DMSO d6) d = 182.33, 155.86, 144.34,143.90, 142.45, 129.68, 129.55, 127.26, 126.19, 123.43, 123.13,116.83, 115.58, 112.93, 52.32, 34.74, 26.52.

Reference： [1]Cai, Yiping; Liu, Chang; Lei, Zhaoxia; Wang, Zhiming; Bian, Yaye; He, Song; Zeng, Xianshun [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 265]

88
tetrafluoroboric acid [ No CAS ]
[ 22304-67-2 ]
[ 5418-63-3 ]
C₃₃H₃₅N₂O₂⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 4,6-dihydroxy-5-methyl-1,3-benzenedicarboxaldehyde; 1,2,3,3-tetramethyl-3H-indolium iodide With piperidine In ethanol at 95℃; for 24h; Sealed tube; Stage #2: tetrafluoroboric acid In ethanol for 2h; Sealed tube;	2.2. Synthesis of the probe DpIn A mixture of compound 1 (45 mg, 0.25 mmol), 1,2,3,3-tetramethyl1indolium Iodide (165 mg, 0.55 mmol) and twodrops piperidine were dissolved in 10 mL EtOH. The reaction mixturewas stirred for 24 h at 95 C under sealed condition. Aftercooling to room temperature, added 150 lL HBF4 and kept stirringScheme 1. The structures of subcellular-targeting cyanines and the synthesis route of the probe DpIn and NaIn. i) a. Formamidine acetate, acetic anhydride, THF, 95 C, 24 h;bH2O, H+. ii) a. EtOH, piperidine; b. HBF4.Y. Cai, C. Liu, Z. Lei et al. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 265 (2022) 1204042 for 2 h. In this progress, the product precipitated as a brown powderand was isolated by filtration and recrystallized from aqueousethanol (70 mg, yield 63%). M.p. 300 C; HRMS: m/z [C33H35N2-O2 + H2O-BF4 - ]+ = 509.2799, calcd for 509.2710. 1H NMR(400 MHz, DMSO d6) d = 8.81 (s, 1H), 8.09 (d, J = 15.2 Hz, 2H),7.76 (d, J = 7.6 Hz, 2H), 7.67 (d, J = 8 Hz, 2H) 7.55-7.51 (m, 4H),7.44 (t, J = 15.2 Hz, 2H), 3.82 (s, 12H), 1.75 (d, J = 3.2 Hz, 12H),1.40 (s, 3H). 13C NMR(100 MHz, DMSO d6) d = 197.89, 179.12,142.72, 142.52, 129.15, 127.29, 123.00, 117.26, 113.44, 104.66,83.30, 50.61, 32.86, 28.43, 27.39, 27.30, 19.03.

Reference： [1]Cai, Yiping; Liu, Chang; Lei, Zhaoxia; Wang, Zhiming; Bian, Yaye; He, Song; Zeng, Xianshun [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2022, vol. 265]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	5418-63-3	MDL No. :	MFCD00013333
Formula :	C₁₂H₁₆IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HCYIOKVZAATOEW-UHFFFAOYSA-M
M.W :	301.17	Pubchem ID :	79454
Synonyms :

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.42
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	76.02
TPSA :	3.01 Å²

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.97 cm/s

Log Po/w (iLOGP) :	-0.28
Log Po/w (XLOGP3) :	3.05
Log Po/w (WLOGP) :	-0.66
Log Po/w (MLOGP) :	3.38
Log Po/w (SILICOS-IT) :	2.56
Consensus Log Po/w :	1.61

[ CAS No. 5418-63-3 ] {[proInfo.proName]}

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[ 5418-63-3 ] Synthesis Path-Upstream 1~5

[ 5418-63-3 ] Synthesis Path-Downstream 1~88

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[ 5418-63-3 ]

Indoles

Precautionary Statements-General

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Physical hazards

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Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.95
Solubility :	0.0341 mg/ml ; 0.000113 mol/l
Class :	Soluble
Log S (Ali) :	-2.78
Solubility :	0.501 mg/ml ; 0.00166 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.52
Solubility :	0.00912 mg/ml ; 0.0000303 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.8

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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Code	Phrase
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Code	Phrase
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Code	Phrase
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P363	Wash contaminated clothing before reuse.
P370	In case of fire:
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P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
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P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 5418-63-3 ] {[proInfo.proName]}

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[ 5418-63-3 ] Synthesis Path-Upstream 1~5

[ 5418-63-3 ] Synthesis Path-Downstream 1~88

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