[ CAS No. 1912-33-0 ] {[proInfo.proName]}

Name: 1912-33-0|Methyl 2-(1H-indol-3-yl)acetate|97%
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3d Animation Molecule Structure of 1912-33-0

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Quality Control of [ 1912-33-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1912-33-0 ]

SDS Specification

Alternatived Products of [ 1912-33-0 ]

Product Details of [ 1912-33-0 ]

CAS No. :	1912-33-0	MDL No. :	MFCD00005636
Formula :	C₁₁H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KTHADMDGDNYQRX-UHFFFAOYSA-N
M.W :	189.21	Pubchem ID :	74706
Synonyms :

Calculated chemistry of [ 1912-33-0 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.16
TPSA :	42.09 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	1.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.39
Solubility :	0.776 mg/ml ; 0.0041 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.09 mg/ml ; 0.00575 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0324 mg/ml ; 0.000171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 1912-33-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1912-33-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 1912-33-0 ]
Downstream synthetic route of [ 1912-33-0 ]

[ 1912-33-0 ] Synthesis Path-Upstream 1~6

1
[ 1912-33-0 ]
[ 4363-93-3 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 11, p. 2109 - 2114

2
[ 1912-33-0 ]
[ 879-37-8 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 650,658

3
[ 1912-33-0 ]
[ 74-88-4 ]
[ 58665-00-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6 h;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65percent); ¹H NMR (400 MHz, CDCl₃): δ 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); ¹³C NMR (100 MHz, CDCl₃): δ 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
19%	Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) for 1 h; Stage #2: for 18 h;	To a suspension of sodium hydride (104 mg, 7.61 [MMOL)] in DMF (11 mL) was added a solution of 1 H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 [MMOL)] in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 [MMOL).] The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3 x 100 mL). The combined organic layers were dried with [NA2SO4,] and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19percent) of [(1-METHYL-1H-INDOL-3-YL)-ACETIC] acid methyl ester after purification. HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for [C12H13NO2,] 203.09 ; m/z found 204.09 [[M+H] +. 1H] NMR (400 MHz, [CDCI3)] : 7.60 (d, J = 7.9 Hz, [1 H),] 7.30 (d, [J =] 8.2 Hz, 1 H), 7.23 (t, J = 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 [(S,] [1 H),] 3.77 (s, 2H), 3.76 (s, [3H),] 3.69 (s, 3H).
19%	Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) for 1 h; Stage #2: for 18 h;	To a suspension of20 sodium hydride (104 mg, 7.61 mmol) in DMF (11 ml) was added a solution of1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 ml). Themixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8mmol). The reaction mixture was stirred for an additional 18 h, quenched,diluted with saturated ammonium chloride (200 ml), and then extracted with25 diethyl ether (3 x 100 ml). The combined organic layers were dried withNasSCU, and the solvent was removed under reduced pressure. The cruderesidue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg(19percent) of (1 -methyl-1 H-indol-3-yl)-acetic acid methyl ester after purification.HPLC: R_t = 8.91 (Method A). MS (ES+): mass calculated for C₁₂H₁₃NO₂, 203.09; m/z found 204.09 [M+Hf. ¹H NMR (400 MHz, CDCI₃): 7.60 (d, J= 7.9Hz, 1H), 7.30 (d, J= 8.2 Hz, 1H), 7.23 (t, J= 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H),7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).

19%	With sodium hydride In DMF (N,N-dimethyl-formamide) for 19 h;	A. (1-Methyl-1H-indol-3-yl)-acetic acid methyl ester. To a suspension of sodium hydride (104 mg, 7.61 mmol) in DMF (11 mL) was added a solution of 1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 mmol). The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3*100 mL). The combined organic layers were dried with Na₂SO₄, and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19percent) of (1-methyl-1H-indol-3-yl)-acetic acid methyl ester after purification. HPLC: R_t=8.91 (Method A). MS (ES+): mass calculated for Cl₂H₁₃NO₂, 203.09; m/z found 204.09 [M+H]⁺. ¹H NMR (400 MHz, CDCl₃): 7.60 (d, J=7.9 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
2.71 g	Stage #1: With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1 h; Stage #2: at 0℃; for 0.25 h;	To a suspension of NaH (ca. 60wtpercent, 728 mg, 18.21 mmol) in THF (30 mL) and DMF (15 mL) at 0 °Cwas added a solution of the crude methyl ester in THF (30 mL) dropwise. After stirring at 0 °C for 1 h,MeI (2.06 mL, 33.11 mmol) was added dropwise. The reaction mixture was stirred at 0 °C for 15 min.The reaction was quenched successively with H2O (2 mL) and sat. aq. NH4Cl (6 mL). The layers wereseparated, and the aqueous layer was extracted with AcOEt (2 x 60 mL). The organic layers werecombined, washed with brine (60 mL), dried over MgSO4, and concentrated in vacuo. The residue waspurified by flash chromatography (silica gel, hexane/AcOEt = 10:1) to afford 26 (2.71 g, 81percent yield from3-indoleacetic acid) as a colorless oil.
1.4 g	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3 h;	To a stirred solution of 2-(1H-indol-3-yl)acetic acid (19-1) (3.0 g, 17.1 mmol) in DMF (20.0 mL ) was added K₂CO₃ (7.09 g, 51.3 mmol) and the reaction mixture was stirred for 15 minutes. Methyl iodide (3.19 mL, 51.3 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 16 hours. TLC showed formation of a new spot (Rf-0.5 in 20percent ethyl acetate/hexane). The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. ¹HNMR and LCMS showed only the acid group was converted to its methyl ester, N-methylation didn't took place. The residue was again dissolved in THF (15.0 mL) and to it was added NaH (1.0 eq) at 0°C. MeI (1.0 eq) was then added to the reaction mixture and the reaction mixture was stirred at room temperature for 3 hours. TLC showed a new spot formation (Rf-0.6 in 10percent ethyl acetate/hexane). The reaction was diluted with cold water and ethyl acetate. The organic layer was separated and washed with water, brine, dried over sodium sulfate, concentrated and the resulting residue was purified by column chromatography (silica 100-200, 0percent-2percent ethyl acetate/hexane) to afford methyl 2-(1-methyl-1H-indol-3-yl)acetate 19-2 (1.40 g, 6.88 mmol, 40.3 percent) as a yellow oil. LC MS: ES+ 204.3.

Reference： [1] Organic letters, 2000, vol. 2, # 17, p. 2639 - 2641
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 20, p. 2374 - 2389
[3] Journal of Organic Chemistry, 1980, vol. 45, # 16, p. 3172 - 3176
[4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[5] Patent: US2015/353489, 2015, A1, . Location in patent: Paragraph 0240; 0241
[6] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722
[7] Patent: WO2004/7463, 2004, A1, . Location in patent: Page 183-184
[8] Patent: WO2005/5393, 2005, A2, . Location in patent: Page/Page column 183-184
[9] Patent: US2006/4195, 2006, A1, . Location in patent: Page/Page column 80
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 2219 - 2224
[11] Organic Letters, 2010, vol. 12, # 21, p. 4956 - 4959
[12] Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112
[13] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[14] Patent: WO2017/197046, 2017, A1, . Location in patent: Page/Page column 303

4
[ 87-51-4 ]
[ 616-38-6 ]
[ 1912-33-0 ]
[ 58665-00-2 ]

Reference： [1] Organic Process Research and Development, 2001, vol. 5, # 6, p. 604 - 608

5
[ 1912-33-0 ]
[ 24424-99-5 ]
[ 370562-34-8 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722
[2] Tetrahedron, 2009, vol. 65, # 44, p. 9015 - 9020
[3] Tetrahedron, 2004, vol. 60, # 44, p. 10039 - 10047
[4] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6149 - 6152
[5] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6595 - 6603
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4329 - 4339
[7] Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 500 - 511
[8] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2111 - 2114

6
[ 1912-33-0 ]
[ 152213-63-3 ]

Reference： [1] Chemistry Letters, 2011, vol. 40, # 10, p. 1079 - 1081

[ 1912-33-0 ] Synthesis Path-Downstream 1~19

1
[ 1912-33-0 ]
[ 526-55-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride In tetrahydrofuran
81%	With isopropyl alcohol In hexane at 0 - 20℃; for 0.583333h; Inert atmosphere;
69%	With tetrabutylammonium borohydride In dichloromethane for 10h; Heating;

	With lithium aluminium tetrahydride; diethyl ether
	With lithium aluminium tetrahydride
	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h;	19 EXAMPLE 19; 1-Acetyl-2,3-dihydro-3-[2-(methanesulphonyl)ethyl]-1H-indole, 19a To a solution of indole-3-acetic acid (100 g) in methanol (1 l) was added ether saturated with HCl (200 ml), and the solution was left at room temperature for 3 hours. The solution as evaporated in vacuo, and the residue was dissolved in THF 1.2 l) and added slowly with cooling to a stirred suspension of LiAlH4 (28.6 g) in THF (1 l). After stirring for 2 hours at room temperature, the mixture was cooled in an ice bath, and water (57 ml), 15% NaOH (29 ml), and water (143 ml) was added. The mixture was filtered and evaporated in vacuo, and the residue (84.9 g) was dissolved in dioxane (1.5 l). Borane trimethylamine complex (200 g) was added, and to the stirred mixture was added concentrated hydrochloric acid (150 ml) during 1 hour. The mixture was heated to 40° C. for 30 minutes and then to reflux for 2.5 hours. Then 6 M hydrochloric acid (460 ml) was added and reflux was continued for 30 minutes. The solution was concentrated in vacuo, and the residue was poured on ice. The solution was washed with ether and was made basic with concentrated NaOH and then extracted with ether. The organic phase was dried over MgSO4 and was evaporated in vacuo. The residue was dissolved in CH2Cl2 (680 ml) and triethylamine (68 ml). Acetyl chloride (36 ml) was added at 5° C. during 1 hour. After further stirring for 1 hour at room temperature, the mixture was washed with dilute hydrochloric acid, and NaHCO3 solution. After drying over MgSO4 and evaporation in vacuo, the residue was dissolved in methanol (500 ml), and 30% Na-methanolat (10 ml) was added. The mixture was stirred for 4 hours at room temperature and was then evaporated in vacuo and was dissolved in CH2Cl2 and was washed with saturated NaCl solution, dried over MgSO4 and evaporation in vacuo. The residue (75.4 g) was dissolved in CH2Cl2 (1 l) and triethylamine (100 ml). With cooling was added a solution of methanesulphonic chloride (27 ml) in CH2Cl2 (175 ml) at 10° C. After stirring for 30 minutes at 0° C. and 1 hour at room temp the mixture was evaporated in vacuo and was purified on silica gel eluted with ethyl acetate to give the title product as an oil (74 g).
72 %Chromat.	Stage #1: Indole-3-acetic acid methyl ester With diethoxymethylane; zinc diacetate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; Stage #2: With methanol; potassium hydroxide chemoselective reaction;
	With diisobutylaluminium hydride In tetrahydrofuran; toluene at 20℃;

Reference： [1]Zarezin, Danil P.; Shmatova, Olga I.; Kabylda, Adil M.; Nenajdenko, Valentine G. [European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722]
[2]An, Jie; Work, D. Neil; Kenyon, Craig; Procter, David J. [Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6743 - 6747]
[3]Wakamatsu, Takeshi; Inaki, Harumi; Ogawa, Akemi; Watanabe, Masako; Ban, Yoshio [Heterocycles, 1980, vol. 14, # 10, p. 1441 - 1444]
[4]Vitali; Mossini [Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 84,86] Fish et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 3668,3670]
[5]Alvarez, Ricardo G.; Hunter, Iain S.; Suckling, Colin J.; Thomas, Michael; Vitinius, Ute [Tetrahedron, 2001, vol. 57, # 40, p. 8581 - 8587]
[6]Current Patent Assignee: H. LUNDBECK A/S - US6352988, 2002, B2 Location in patent: Page column 28-29
[7]Location in patent: experimental part Das, Shoubhik; Moeller, Konstanze; Junge, Kathrin; Beller, Matthias [Chemistry - A European Journal, 2011, vol. 17, # 27, p. 7414 - 7417]
[8]Location in patent: experimental part Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]

2
[ 1912-33-0 ]
[ 879-37-8 ]

Reference： [1]Journal of the Chemical Society,1952,p. 650,658

3
[ 1912-33-0 ]
[ 5448-47-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrazine hydrate In methanol at 60℃;	3.1 Example 3: 2-(5-((lH-indol-3-yl)methyl)-4-butyl-4H-l,2,4-triazol-3-yl)-5-(4-methylpiperazin- l-yl)-l,3,4-thiadiazole. 0115] Step 1. General procedure for preparation of Intermediate 15. 15 A solution of methyl 2-(lH-indol-3-yl)acetate (20.0 g, 0.106 mol), and ΝΗ2ΝΗ2·Η20 (12.5 g, 0.53 mol) in MeOH (200 mL) was stirred at 60 °C overnight. TLC Rf 0.5 (petroleum ether/EtOAc, 4/1) showed the reaction was complete. The reaction mixture was concentrated and CH2CI2 was added to the residue to recrystallize the product. The mixture was filtered and the filter cake was dried by vacuum at 50 °C to give Intermediate 15 (20 g, 100%) as yellow solid. 1H NMR (400 MHz, MeOD) δ 3.61 (s, 2H), 6.99-7.02 (m, 1H), 7.07-7.11 (m, 1H), 7.15 (s, 1H), 7.32-7.34 (d, J = 8.4 Hz, 1H), 7.53-7.55 (d, J = 8.0 Hz, 1H).
87%	With hydrazine hydrate Microwave irradiation;	Microwave-assisted synthesis of intermediate 3 General procedure: Compound 2 (5 mmol) was added to hydrazine- hydrate (80) (3 mL)at room temperature, and the mixture was irradiated continually for 5-8 min at 300 W. The reaction progress was monitored by TLC. After the reaction was complete and the mixture was sufficiently cooled, intermediate 3 (yield 83-98) was formed.
85%	With hydrazine In methanol

68%	With hydrazine hydrate In ethanol for 28h; Heating;
66%	With hydrazine hydrate In ethanol for 6h; Heating;
60%	With hydrazine In ethanol Reflux;
59%	With hydrazine hydrate In ethanol Heating;
	With water; hydrazine hydrate
	With ethanol; hydrazine hydrate
9.2 g	With hydrazine hydrate In 1,2-dimethoxyethane at 115℃; for 20h;	1.2 (2) in a 500 ml round bottom flask methyl indole acetic acid is added in 9.46g (48mmol), ethylene glycol monomethyl ether (40 ml), 5 ml of hydrazine hydrate, 115 °C heating reflux reaction about 20 hours, thin layer chromatography (TLC) detecting raw material point dematerialised, stop the reaction, cooling to room temperature, adding water (50 ml), static separating white solid, filtering to get the crude product, using ethanol is recrystallized to get indole acetic acid hydrazide white solid 9.2 g.
	With hydrazine hydrate In ethanol for 3h; Reflux;
	With hydrazine hydrate In methanol; water for 16h; Reflux;
	With hydrazine hydrate In methanol for 6h; Reflux;	4.2. General procedure for the synthesis of indolederivatives (1-22) Indole derivatives were synthesized by refluxing methyl 2-(1H-indol-3-yl) acetate (5 mmol) with hydrazine hydrate (5 mL) in methanol (15 mL) for 6 hrs yielded 2-(1H-indol-3-yl)acetohydrazide as intermediate product (I). The completionof reaction was monitored using TLC. The excess solventwere evaporated under vacuum to obtain the crude productand recrystallized in methanol to obtained pure product.Equimolar intermediate product (I) then further treated withdifferent aldehydes (1-22) in methanol (15 mL) for 3-4 hrs inthe presence of catalytic amount of acetic acid yieldedindole derivatives (1-22). The completion of reaction wasmonitored with the help of TLC. The crude was then recrystallizedin methanol to obtained pure product (Hanna et al.,2007; Ju et al., 2019; Liu et al., 2019; Mirfazli et al., 2016). 4.3. 2-(1h-indol-3-yl)-N’-(4-nitrobenzylidene)acetohydrazide (1)Yield: (88%); mp 289-291 C match (Hanna et al., 2007; Juet al., 2019; Liu et al., 2019; Mirfazli et al., 2016); 1HNMR;(400 MHz, DMSO-d6): d 11.70 (s, 1H, NH), 11.52 (s, 1H, NH),8.70 (s, 1H), 8.36 (d, 2H, J8.0 Hz), 7.89 (d, 2H, J8.0 Hz),7.60 (t, 1H, J7.0 Hz), 7.22 (d, 1H, J7.5 Hz), 6.92-6.86 (m,3H), 3.69 (s, 2H, CH2);13CNMR (100, MHz, DMSO) d171.0,150.5, 144.3, 139.5, 136.3, 127.2, 125.0, 125.0, 124.2,124.2, 123.5, 121.4, 119.5,118.6, 111.2, 109.5, 36.0, HR-EIMSm/z, calcd for C17H14N4O3 [M] 322.1066 found 322.1053.

Reference： [1]Current Patent Assignee: UCB - WO2014/14937, 2014, A1 Location in patent: Paragraph 0115
[2]Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan [Journal of Chemical Research, 2015, vol. 39, # 5, p. 296 - 299]
[3]Yar, Muhammad; Bajda, Marek; Mehmood, Rana Atif; Sidra, Lala Rukh; Ullah, Nisar; Shahzadi, Lubna; Ashraf, Muhammad; Ismail, Tayaba; Shahzad, Sohail Anjum; Khan, Zulfiqar Ali; Naqvi, Syed Ali Raza; Mahmood, Nasir [Letters in drug design and discovery, 2014, vol. 11, # 3, p. 331 - 338]
[4]Khan, Khalid Mohammed; Rahat, Shagufta; Choudhary, Muhammad Iqbal; Atta-ur-Rahman; Ghani, Usman; Perveen, Shahnaz; Khatoon, Shagufta; Dar, Ahsana; Malik, Abdul [Helvetica Chimica Acta, 2002, vol. 85, # 2, p. 559 - 570]
[5]Kelarev; Shvekhgeimer [Chemistry of Heterocyclic Compounds, 1982, vol. 18, # 3, p. 258 - 261]
[6]Yar, Muhammad; Sidra, Lala Rukh; Pontiki, Eleni; Mushtaq, Nafeesa; Ashraf, Muhammad; Nasar, Rumana; Khan, Islam Ullah; Mahmood, Nasir; Naqvi, Syed Ali Raza; Khan, Zulfiqar Ali; Shahzad, Sohail Anjum [Journal of the Iranian Chemical Society, 2014, vol. 11, # 2, p. 369 - 378]
[7]Demange, Luc; Boeglin, Damien; Moulin, Aline; Mousseaux, Delphine; Ryan, Joanne; Bergé, Gilbert; Gagne, Didier; Heitz, Annie; Perrissoud, Daniel; Locatelli, Vittorio; Torsello, Antonio; Galleyrand, Jean-Claude; Fehrentz, Jean-Alain; Martinez, Jean [Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1939 - 1957]
[8]Katritzky [Journal of the Chemical Society, 1955, p. 2586,2591] Yale et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1933,1934] Tanaka [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 362,365; dtsch. Ref. S. 143][Chem.Abstr., 1941, p. 1481]
[9]Katritzky [Journal of the Chemical Society, 1955, p. 2586,2591] Yale et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1933,1934] Tanaka [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 362,365; dtsch. Ref. S. 143][Chem.Abstr., 1941, p. 1481]
[10]Current Patent Assignee: YUNNAN UNIVERSITY; KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105732468, 2016, A Location in patent: Paragraph 0068
[11]Eldehna, Wagdy M.; Hassan, Ghada S.; Al-Rashood, Sara T.; Alkahtani, Hamad M.; Almehizia, Abdulrahman A.; Al-Ansary, Ghada H. [Marine Drugs, 2020, vol. 18, # 4]
[12]Iškauskienė, Monika; Kadlecová, Alena; Voller, Jiří; Janovská, Lucie; Malinauskienė, Vida; Žukauskaitė, Asta; Šačkus, Algirdas [Archiv der Pharmazie, 2021, vol. 354, # 6]
[13]Taha, Muhammad; Ismail, Sukinah; Imran, Syahrul; Almandil, Noor Barak; Alomari, Munther; Rahim, Fazal; Uddin, Nizam; Hayat, Shawkat; Zaman, Khalid; Ibrahim, Mohamad; Alghanem, Bandar; Islam, Imadul; Farooq, Rai Khalid; Boudjelal, Mohamed; Khan, Khalid Mohammed [Journal of Biomolecular Structure and Dynamics, 2021]

4
[ 85676-99-9 ]
[ 17697-12-0 ]
[ 1912-33-0 ]
[ 1666-13-3 ]
(2-Phenylselanyl-1H-indol-3-yl)-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 29% 2: 89%	In tetrahydrofuran for 2h;

Reference： [1]Barton, Derek H. R.; Lusinchi, Xavier; Milliet, Pierre [Tetrahedron, 1985, vol. 41, # 21, p. 4727 - 4738]

5
[ 1912-33-0 ]
[ 74-88-4 ]
[ 58665-00-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 6h;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65%); 1H NMR (400 MHz, CDCl3): delta 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
65%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65%); 1H NMR (400 MHz, CDCl3): delta 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
19%		To a suspension of sodium hydride (104 mg, 7.61 [MMOL)] in DMF (11 mL) was added a solution of 1 H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 [MMOL)] in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 [MMOL).] The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3 x 100 mL). The combined organic layers were dried with [NA2SO4,] and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19%) of [(1-METHYL-1H-INDOL-3-YL)-ACETIC] acid methyl ester after purification. HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for [C12H13NO2,] 203.09 ; m/z found 204.09 [[M+H] +. 1H] NMR (400 MHz, [CDCI3)] : 7.60 (d, J = 7.9 Hz, [1 H),] 7.30 (d, [J =] 8.2 Hz, 1 H), 7.23 (t, J = 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 [(S,] [1 H),] 3.77 (s, 2H), 3.76 (s, [3H),] 3.69 (s, 3H).

19%		To a suspension of20 sodium hydride (104 mg, 7.61 mmol) in DMF (11 ml) was added a solution of1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 ml). Themixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8mmol). The reaction mixture was stirred for an additional 18 h, quenched,diluted with saturated ammonium chloride (200 ml), and then extracted with25 diethyl ether (3 x 100 ml). The combined organic layers were dried withNasSCU, and the solvent was removed under reduced pressure. The cruderesidue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg(19%) of (1 -methyl-1 H-indol-3-yl)-acetic acid methyl ester after purification.HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for C12H13NO2, 203.09; m/z found 204.09 [M+Hf. 1H NMR (400 MHz, CDCI3): 7.60 (d, J= 7.9Hz, 1H), 7.30 (d, J= 8.2 Hz, 1H), 7.23 (t, J= 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H),7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
19%	With sodium hydride; In DMF (N,N-dimethyl-formamide); for 19h;	A. (1-Methyl-1H-indol-3-yl)-acetic acid methyl ester. To a suspension of sodium hydride (104 mg, 7.61 mmol) in DMF (11 mL) was added a solution of 1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 mmol). The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3*100 mL). The combined organic layers were dried with Na2SO4, and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19%) of (1-methyl-1H-indol-3-yl)-acetic acid methyl ester after purification. HPLC: Rt=8.91 (Method A). MS (ES+): mass calculated for Cl2H13NO2, 203.09; m/z found 204.09 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.60 (d, J=7.9 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
2.71 g		To a suspension of NaH (ca. 60wt%, 728 mg, 18.21 mmol) in THF (30 mL) and DMF (15 mL) at 0 Cwas added a solution of the crude methyl ester in THF (30 mL) dropwise. After stirring at 0 C for 1 h,MeI (2.06 mL, 33.11 mmol) was added dropwise. The reaction mixture was stirred at 0 C for 15 min.The reaction was quenched successively with H2O (2 mL) and sat. aq. NH4Cl (6 mL). The layers wereseparated, and the aqueous layer was extracted with AcOEt (2 x 60 mL). The organic layers werecombined, washed with brine (60 mL), dried over MgSO4, and concentrated in vacuo. The residue waspurified by flash chromatography (silica gel, hexane/AcOEt = 10:1) to afford 26 (2.71 g, 81% yield from3-indoleacetic acid) as a colorless oil.
1.4 g	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 3h;	To a stirred solution of 2-(1H-indol-3-yl)acetic acid (19-1) (3.0 g, 17.1 mmol) in DMF (20.0 mL ) was added K2CO3 (7.09 g, 51.3 mmol) and the reaction mixture was stirred for 15 minutes. Methyl iodide (3.19 mL, 51.3 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 16 hours. TLC showed formation of a new spot (Rf-0.5 in 20% ethyl acetate/hexane). The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. 1HNMR and LCMS showed only the acid group was converted to its methyl ester, N-methylation didn't took place. The residue was again dissolved in THF (15.0 mL) and to it was added NaH (1.0 eq) at 0C. MeI (1.0 eq) was then added to the reaction mixture and the reaction mixture was stirred at room temperature for 3 hours. TLC showed a new spot formation (Rf-0.6 in 10% ethyl acetate/hexane). The reaction was diluted with cold water and ethyl acetate. The organic layer was separated and washed with water, brine, dried over sodium sulfate, concentrated and the resulting residue was purified by column chromatography (silica 100-200, 0%-2% ethyl acetate/hexane) to afford methyl 2-(1-methyl-1H-indol-3-yl)acetate 19-2 (1.40 g, 6.88 mmol, 40.3 %) as a yellow oil. LC MS: ES+ 204.3.

Reference： [1]Organic letters,2000,vol. 2,p. 2639 - 2641
[2]Tetrahedron Asymmetry,2009,vol. 20,p. 2374 - 2389
[3]Journal of Organic Chemistry,1980,vol. 45,p. 3172 - 3176
[4]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2843 - 2866
[5]Patent: US2015/353489,2015,A1 .Location in patent: Paragraph 0240; 0241
[6]Patent: US2019/224165,2019,A1 .Location in patent: Paragraph 0093; 0094; 0219-0220
[7]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722
[8]Patent: WO2004/7463,2004,A1 .Location in patent: Page 183-184
[9]Patent: WO2005/5393,2005,A2 .Location in patent: Page/Page column 183-184
[10]Patent: US2006/4195,2006,A1 .Location in patent: Page/Page column 80
[11]Journal of the Chemical Society. Perkin transactions I,1983,p. 2219 - 2224
[12]Organic Letters,2010,vol. 12,p. 4956 - 4959
[13]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2101 - 2112
[14]Tetrahedron,2013,vol. 69,p. 9481 - 9493
[15]Patent: WO2017/197046,2017,A1 .Location in patent: Page/Page column 303

6
[ 1912-33-0 ]
[ 2591-98-2 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 2109 - 2114
[2]Journal of the American Chemical Society,2008,vol. 130,p. 933 - 944
[3]Synthesis,2011,p. 2935 - 2940
[4]Chemistry - An Asian Journal,2016,vol. 11,p. 390 - 394
[5]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722

7
[ 700-06-1 ]
[ 1912-33-0 ]
[ 114648-66-7 ]
[ 92001-33-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1984,p. 1578 - 1586

8
[ 1912-33-0 ]
[ 24424-99-5 ]
[ 370562-34-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;	As shown in Fig. 24K, to a solution of compound 1 (20 g, 0.106 mol, 1.0 eq) in DCM (20 mL) was successively added B C O (24.4 g, 0.112 mol, 1.056 eq), DMAP (646 mg, 5.29 mmol, 0.05 eq) and TEA (534 mg, 5.29 mmol, 0.05 eq). The mixture was stirred at room temperature for 16 h. TLC analysis of the reaction mixture showed full conversion to the desired product. Then the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography to afford compound 2 (24 g, 78%).

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722
[2]Tetrahedron,2009,vol. 65,p. 9015 - 9020
[3]Tetrahedron,2004,vol. 60,p. 10039 - 10047
[4]Patent: WO2019/200232,2019,A1 .Location in patent: Paragraph 0932
[5]Tetrahedron Letters,2000,vol. 41,p. 6149 - 6152
[6]Journal of Organic Chemistry,2001,vol. 66,p. 6595 - 6603
[7]Journal of Medicinal Chemistry,2007,vol. 50,p. 4329 - 4339
[8]Journal of Organic Chemistry,2011,vol. 76,p. 500 - 511
[9]Journal of Organic Chemistry,2014,vol. 79,p. 2111 - 2114

9
[ 87-51-4 ]
[ 1912-33-0 ]
[ 58665-00-2 ]
[ 616-38-6 ]
[ 23304-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Example 17 Preparation of 1-methylindole-3acetic acid methyl ester and 1-indole-3-acetic acid methyl ester. To a three-necked round bottom flask was charged indole-3-acetic acid (3.0 g, 17.12 mmol), potassium carbonate (powder, 1.5 g), N,N-dimethylformamide (20 mL) and dimethyl carbonate (4.3 mL, 51.07 mmol). The resulting mixture was heated to reflux (~130 C.) for 6 h at which time analysis of the reaction by HPLC indicated the starting material had been consumed. After the reaction mixture was cooled to room temperature, it was partitioned between water (50 mL) and tert-butyl methyl ether (60 mL). The separated organic layer was washed with water (2*50 mL) and the solvent was evaporated under reduced pressure. The crude product, shown by HPLC analysis to contain 1-methylindole-3-acetic acid methyl ester (89%) and 1-indole-3-acetic acid methyl ester (8%), was separated into the individual components by using column chromatography over silica gel. Total yield 3.2 g, 2.8 g for 1-methylindole-3-acetic acid methyl ester and 0.40 g for 1-indole-3-acetic acid methyl ester.

Reference： [1]Patent: US6326501,2001,B1

10
[ 67-56-1 ]
[ 526-55-6 ]
[ 1912-33-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With water; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 24h;

Reference： [1]Owston, Nathan A.; Parker, Alexandra J.; Williams, Jonathan M. J. [Chemical Communications, 2008, vol. 8, # 5, p. 624 - 625]

11
[ 1912-33-0 ]
[ 152213-63-3 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 1079 - 1081

12
[ 1912-33-0 ]
[ 1218918-62-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 2299 - 2309

13
[ 19213-72-0 ]
[ 1912-33-0 ]
[ 157496-76-9 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 8304 - 8308

14
[ 1912-33-0 ]
[ 2532-74-3 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 9481 - 9493

15
[ 87-51-4 ]
[ 616-38-6 ]
[ 1912-33-0 ]
[ 58665-00-2 ]

Reference： [1]Organic Process Research and Development,2001,vol. 5,p. 604 - 608

16
[ 87-51-4 ]
[ 119-36-8 ]
[ 1912-33-0 ]
[ 69-72-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: indole-3-acetic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h;	Methyl 2-Methoxybenzoate (3a); Typical Procedure General procedure: A mixture of 2-methoxybenzoic acid (3.8 g, 25 mmol) and K2CO3 (2.07 g, 15 mmol) in DMA (50 mL) was stirred at 110 °C for 0.5 h. Methyl salicylate (5.70 g, 37.5 mmol) was added and the resulting mixture was stirred for 24 h. The solvent was then removed in vacuo. After cooling to r.t., K2CO3 (2.42 g, 17.5 mmol) and water (50mL) were added to hydrolyze the excess methyl salicylate. The resulting mixture was heated at 60 °C until methyl salicylate disappeared on TLC. Then, the solution was extracted with EtOAc (3 ×20 mL). The organic layer was washed with water, sat. aq NaCl solution,and dried (anhyd MgSO4). Evaporation of solvent in vacuoafforded methyl 2-methoxybenzoate (3.82 g, 92%). More than 90% of salicylic acid was recovered as a white precipitate by acidifying the aqueous phase with 1 M HCl.

Reference： [1]Chen, Si; Jia, Lei; Li, Xiaonan; Luo, Meiming [Synthesis, 2014, vol. 46, # 2, p. 263 - 268]

17
[ 1912-33-0 ]
[ 638-45-9 ]
N-hexyl-3-indoleacetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	1 N-Hexyl-3-indoleacetic acid methyl ester N-Hexyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Hexyl-3-indoleacetic acid methyl ester N-Hexyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Hexyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.

With hydrogenchloride

N-Hexyl-3-indoleacetic Acid Methyl Ester N-Hexyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - US2015/353489, 2015, A1 Location in patent: Paragraph 0256; 0257
[2]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2019/224165, 2019, A1 Location in patent: Paragraph 0093; 0094; 0235-0236
[3]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1 Location in patent: Paragraph 0084-0085; 0228-0229
[4]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1

18
[ 1912-33-0 ]
[ 4282-40-0 ]
N-heptyl-3-indoleacetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	1 N-Heptyl-3-indoleacetic acid methyl ester N-Heptyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl4): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Heptyl-3-indoleacetic acid methyl ester N-Heptyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Heptyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.

With hydrogenchloride

N-Heptyl-3-indoleacetic Acid Methyl Ester N-Heptyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - US2015/353489, 2015, A1 Location in patent: Paragraph 0260; 0261
[2]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2019/224165, 2019, A1 Location in patent: Paragraph 0093; 0094; 0239-0240
[3]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1 Location in patent: Paragraph 0084-0085; 0232-0233
[4]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1

19
[ 67-56-1 ]
[ 1912-33-0 ]
[ 558-13-4 ]
[ 156362-00-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With Ru(2,2'-bipyridine)3(PF₆)2*H₂O; diisopropylamine at 20℃; for 21h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Yang, Qing-Qing; Marchini, Marianna; Xiao, Wen-Jing; Ceroni, Paola; Bandini, Marco [Chemistry - A European Journal, 2015, vol. 21, # 50, p. 18052 - 18056]

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H401	Toxic to aquatic life
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H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1912-33-0 ] {[proInfo.proName]}

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[ 1912-33-0 ] Synthesis Path-Upstream 1~6

[ 1912-33-0 ] Synthesis Path-Downstream 1~19

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