[ CAS No. 830-93-3 ] {[proInfo.proName]}

Name: 830-93-3|1-(5-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine|98%
Brand: Ambeed
SKU: A288062
Rating: 93 (32 reviews)

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3d Animation Molecule Structure of 830-93-3

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Quality Control of [ 830-93-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 830-93-3 ]

SDS Specification

Alternatived Products of [ 830-93-3 ]

Product Details of [ 830-93-3 ]

CAS No. :	830-93-3	MDL No. :	MFCD00055980
Formula :	C₁₁H₁₃BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FSERHDPEOFYMMK-UHFFFAOYSA-N
M.W :	253.14	Pubchem ID :	13249
Synonyms :		Chemical Name :	1-(5-Bromo-1H-indol-3-yl)-N,N-dimethylmethanamine

Calculated chemistry of [ 830-93-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.27
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.47
TPSA :	19.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	2.58
Log Po/w (WLOGP) :	2.84
Log Po/w (MLOGP) :	2.24
Log Po/w (SILICOS-IT) :	3.07
Consensus Log Po/w :	2.63

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.38
Solubility :	0.106 mg/ml ; 0.000418 mol/l
Class :	Soluble
Log S (Ali) :	-2.63
Solubility :	0.596 mg/ml ; 0.00235 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.66
Solubility :	0.00559 mg/ml ; 0.0000221 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.7

Safety of [ 830-93-3 ]

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:

Application In Synthesis of [ 830-93-3 ]

* 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 [ 830-93-3 ]
Downstream synthetic route of [ 830-93-3 ]

[ 830-93-3 ] Synthesis Path-Upstream 1~3

1
[ 830-93-3 ]
[ 40432-84-6 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112

2
[ 830-93-3 ]
[ 142273-20-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112

3
[ 830-93-3 ]
[ 152213-63-3 ]

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112

[ 830-93-3 ] Synthesis Path-Downstream 1~98

1
[ 830-93-3 ]
[ 6326-44-9 ]
[ 15589-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; toluene

Reference： [1]Harvey [Journal of the Chemical Society, 1959, p. 473]

2
[ 87-52-5 ]
[ 830-93-3 ]
[ 59609-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In acetic acid for 20h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Franzone, Jose Sebastian; Cirillo, Rocco; Cravanzola, Carlo [European Journal of Medicinal Chemistry, 1983, vol. 18, # 3, p. 261 - 268]

3
[ 830-93-3 ]
[ 79-46-9 ]
[ 837-87-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With sodium hydroxide for 18h; Heating;

Reference： [1]Kreighbaum; Matier; Dennis; Minielli; Deitchman; Perhach Jr.; Comer [Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 285 - 289]

4
[ 830-93-3 ]
3-dimethylaminomethylindole-5-D [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; water-d2; tert.-butyl lithium Yield given. Multistep reaction;

Reference： [1]Fatum, Tine M.; Anthoni, Uffe; Christophersen, Carsten; Nielsen, Per H. [Heterocycles, 1994, vol. 38, # 7, p. 1619 - 1626]

Yield	Reaction Conditions	Operation in experiment
	/BRN= 160256/;
	Bromindol, HCHO/(CH3)2NH;

6
[ 10075-50-0 ]
[ 50-00-0 ]
[ 124-40-3 ]
[ 830-93-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With acetic acid In 1,4-dioxane; water at 0 - 20℃;	8.1 1. To round bottom flask was charged sequentially with 1,4-dioxane (52 mL), acetic acid (52 mL), 37% wt. aqueous formaldehyde (4 mL, 54 mmol), and H20 (4 mL). Then, 40% wt. aqueous dimethyl amine (7.1 mL, 56 mmol) was added at 0 °C. To this cooled solution was added a solution of 5-bromo-lH-indole (10 g, 51 mmol) in 1,4-dioxane (52 mL) slowly. After 2hr at 0 °C, the reaction mixture was stirred at RT for overnight. The reaction mixture was diluted with H20 (640 mL) and 2M NaOH (500 mL). The resulting precipitate was filtered, and washed with H20 (3 x 200 mL), Hexanes (200 mL). The collected solid was dried under vacuum to give l-(5-bromo-lH-indol-3-yl)-N,N-dimethylmethanamine (12.5 g, 97%). H NMR (400 MHz, DMSO-i δ ppm: 11.12 (s, 1H), 7.72 (s, 1H), 7.30 (d, J=8.4 Hz, 1H), 7.24 (s, 1H), 7.15 (dd, J=8.8, 2.0 Hz, 1H), 3.46 (s, 2H), 2.10 (s, 6H).
90%	Stage #1: 5-bromo-1H-indole; formaldehyd; dimethyl amine With acetic acid In tetrahydrofuran; 1,4-dioxane; water at 0 - 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In tetrahydrofuran; 1,4-dioxane; water
90%	With acetic acid In 1,4-dioxane; water at 0 - 20℃; for 14h; Inert atmosphere;

80%	Stage #1: formaldehyd; dimethyl amine In water; acetic acid for 0.166667h; Inert atmosphere; Schlenk technique; Stage #2: 5-bromo-1H-indole In water; acetic acid at 0 - 20℃; Inert atmosphere; Schlenk technique;
	In acetic acid at 20℃; for 12h;
	Acidic conditions;
	With acetic acid In tetrahydrofuran; 1,4-dioxane; water at 0 - 20℃;
	Stage #1: formaldehyd; dimethyl amine With acetic acid In tetrahydrofuran; 1,4-dioxane; water at 0℃; for 0.0833333h; Schlenk technique; Inert atmosphere; Stage #2: 5-bromo-1H-indole In tetrahydrofuran; 1,4-dioxane; water at 0 - 20℃; Schlenk technique; Inert atmosphere;
	Stage #1: formaldehyd; dimethyl amine With acetic acid In 1,4-dioxane; water at 0℃; for 0.25h; Inert atmosphere; Schlenk technique; Stage #2: 5-bromo-1H-indole In 1,4-dioxane; water at 0 - 20℃; for 18h; Inert atmosphere; Schlenk technique;
	In water; acetic acid at 0 - 23℃; for 16.25h;

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1 Location in patent: Paragraph 0133
[2]Bandini, Marco; Eichholzer, Astrid [Angewandte Chemie - International Edition, 2009, vol. 48, # 50, p. 9533 - 9537]
[3]Li, Shi-Guang; Zard, Samir Z. [Organic Letters, 2013, vol. 15, # 22, p. 5898 - 5901]
[4]Lajarín-Cuesta, Rocío; Nanclares, Carmen; Arranz-Tagarro, Juan-Alberto; González-Lafuente, Laura; Arribas, Raquel L.; Araujo De Brito, Monique; Gandía, Luis; De Los Ríos, Cristóbal [Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6265 - 6280]
[5]Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude [Heterocycles, 2003, vol. 60, # 4, p. 865 - 877]
[6]Lu, Aidang; Wang, Tienan; Hui, Hao; Wei, Xiaoye; Cui, Weihao; Zhou, Chunlv; Li, Hongyan; Wang, Ziwen; Guo, Jincheng; Ma, Dejun; Wang, Qingmin [Journal of Agricultural and Food Chemistry, 2019, vol. 67, # 8, p. 2148 - 2156]
[7]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]
[8]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 23, p. 9672 - 9676]
[9]Becker, Antonia; Breit, Bernhard; Grugel, Christian P. [Organic Letters, 2021, vol. 23, # 9, p. 3788 - 3792]
[10]Nair, Vaishnavi N.; Kojasoy, Volga; Laconsay, Croix J.; Kong, Wang Yeuk; Tantillo, Dean J.; Tambar, Uttam K. [Journal of the American Chemical Society, 2021, vol. 143, # 24, p. 9016 - 9025]

7
[ 830-93-3 ]
[ 74-88-4 ]
(5-bromo-1<i>H</i>-indol-3-ylmethyl)-trimethyl-ammonium; iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran at 20℃; for 12h;
	In ethanol at 25℃; for 14h; Inert atmosphere;

Reference： [1]Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude [Heterocycles, 2003, vol. 60, # 4, p. 865 - 877]
[2]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

8
[ 830-93-3 ]
[ 774-14-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrahydrofuran / 12 h / 20 °C 2: 1.86 g / aq. sodium hydroxide / 12 h / 80 °C

Reference： [1]Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude [Heterocycles, 2003, vol. 60, # 4, p. 865 - 877]

9
[ 830-93-3 ]
[ 562823-24-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 12 h / 20 °C 2.1: 1.86 g / aq. sodium hydroxide / 12 h / 80 °C 3.1: bis(pinacolato)diborane; potassium acetate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / dimethylformamide / 2 h / 80 °C 3.2: 53 percent / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); Na₂CO₃ / dimethylformamide / 80 °C

Reference： [1]Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude [Heterocycles, 2003, vol. 60, # 4, p. 865 - 877]

10
[ 830-93-3 ]
N-{2-[3'-(2-acetylaminoethyl)-1H,1'H-[5,5']biindol-3-yl]ethyl}acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrahydrofuran / 12 h / 20 °C 2.1: 1.86 g / aq. sodium hydroxide / 12 h / 80 °C 3.1: bis(pinacolato)diborane; potassium acetate; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) / dimethylformamide / 2 h / 80 °C 3.2: 53 percent / [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); Na₂CO₃ / dimethylformamide / 80 °C 4.1: 67 percent / hydrogen; sodium acetate / Raney nickel / 4 h / 60 °C

Reference： [1]Guillard, Jerome; Larraya, Carlos; Viaud-Massuard, Marie-Claude [Heterocycles, 2003, vol. 60, # 4, p. 865 - 877]

11
[ 830-93-3 ]
[ 833-04-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 68 percent / NaOH / 18 h / Heating 2: 99 percent / 85percent hydrazine hydrate, Raney nickel / ethanol / 2 h / Heating

Reference： [1]Kreighbaum; Matier; Dennis; Minielli; Deitchman; Perhach Jr.; Comer [Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 285 - 289]

12
[ 830-93-3 ]
[ 77216-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 68 percent / NaOH / 18 h / Heating 2: 99 percent / 85percent hydrazine hydrate, Raney nickel / ethanol / 2 h / Heating 3: 0.5 h / 120 - 140 °C

Reference： [1]Kreighbaum; Matier; Dennis; Minielli; Deitchman; Perhach Jr.; Comer [Journal of Medicinal Chemistry, 1980, vol. 23, # 3, p. 285 - 289]

13
[ 830-93-3 ]
[ 6548-09-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOH; toluene 2: aq.-ethanolic NaOH / anschliessend Erhitzen des Reaktionsgemisches mit Essigsaeure

Reference： [1]Harvey [Journal of the Chemical Society, 1959, p. 473]

14
[ 830-93-3 ]
[ 113679-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaOH; toluene 2: aq.-ethanolic NaOH / anschliessend Erhitzen des Reaktionsgemisches mit Essigsaeure 3: aqueous H₂SO₄

Reference： [1]Harvey [Journal of the Chemical Society, 1959, p. 473]

15
[ 830-93-3 ]
[ 7677-24-9 ]
[ 74-88-4 ]
[ 774-14-1 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tetrabutyl ammonium fluoride In tetrahydrofuran; hexane; water; ethyl acetate; benzene	63.2 (5-Bromo-1H-indol-3-yl)-acetonitrile Step 2 (5-Bromo-1H-indol-3-yl)-acetonitrile To an ice cooled suspension of (5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine (11.2 g, 44.1 mmol) in benzene (145 mL) was added iodomethane (8.2 mL, 130 mmol). The reaction mixture was stirred overnight at room temperature and concentrated. The residue was dissolved in THF (210 mL). Trimethylsilyl cyanide (11.7 mL, 87.7 mmol) and tetrabutylammonium fluoride (140 mL, 140 mmol of a 1.0 M solution in THF) were added. After stirring for 2.5 hours, at room temperature, water (12 mL) was added. The mixture was partially concentrated. The residue was partitioned in ethyl acetate and water. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated to dryness. Purification by flash chromatography using 15-35% ethyl acetate in hexane as an eluant afforded (5-bromo-1H-indol-3-yl)-acetonitrile (5.30 g, 51%) as a mauve solid, mp 105-106° C. 1H-NMR (300 MHz, DMSO-d6): δ11.35 (s, 1H), 7.8 (d, 1H, J=2.2 Hz), 7.35-7.45 (m, 2H), 7.2-7.3 (m, 1H), and 4.0 ppm (s, 2H).

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/125371, 2003, A1

16
[ 10075-50-0 ]
aqueous dimethylamine [ No CAS ]
[ 830-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With formaldehyd; acetic acid	63.1 (5-Bromo-1H-indol-3-ylmethyl)-dimethyl-amine Step 1 (5-Bromo-1H-indol-3-ylmethyl)-dimethyl-amine To a mixture of 40% aqueous dimethylamine (5.95 g, 52.8 mmol), 37% aqueous formaldehyde (4.21 g, 51.9 mmol) and acetic acid (7 mL) was added 5-bromo-1H-indole (9.79 g, 49.9 mmol). The reaction mixture was stirred for 21 hours at room temperature and poured into a 2.5 N sodium hydroxide/ice mixture (200 mL). This was extracted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and evaporated to dryness. It was dried at 60° C. for 30 minutes to yield (5-bromo-1H-indol-3-ylmethyl)-dimethyl-amine (11.2 g) as a brown solid: mp 160-162° C. 1H-NMR (200 MHz, DMSO-d6): δ11.1 (br s, 1H), 7.75 (s, 1H), 7.15-7.35 (m, 3H), and 3.5 ppm (s, 2H).
	With formaldehyd; acetic acid In 1,4-dioxane	Procedure 71B. 5-BROMOGRAMINE Procedure 71B. 5-BROMOGRAMINE This material was prepared by the method of Procedure 67B from 49.5 g. of 5-bromoindole, 20 ml. of 37% aqueous formaldehyde, 55 ml. of 25% aqueous dimethylamine, 250 ml. of acetic acid and 250 ml. of dioxane; yield 60.6 g., m.p. 154°-156° C. The structure was confirmed by examination of the NMR spectrum.

Reference： [1]Current Patent Assignee: PFIZER INC - US2003/125371, 2003, A1
[2]Current Patent Assignee: RECKITT BENCKISER GROUP PLC - US4234595, 1980, A

17
[ 10075-50-0 ]
[ 124-40-3 ]
[ 830-93-3 ]

Yield	Reaction Conditions	Operation in experiment
94%	In 1,4-dioxane; formaldehyd; water; acetic acid at 0℃; for 14h;	2 A 1000 ml 5 three-necked round bottom flask equipped with a thermometer, magnetic stir bar and a dropping addition funnel was charged sequentially with 1,4-dioxane (52 ml), 17 M acetic acid (52 ml), 37% wt. aqueous formaldehyde (4.0 ml, 5.4 mmol), and H2O (4.0 ml). The flask was immersed in a NaCl / ice bath and 40% wt. aqueous dimethyl amine (7.1 ml, 56 mmol) was added at once with 0 stirring. To this cooled solution was added a solution of 5-bromoindole (10.0 g, 51.0 mmol) in 1,4-dioxane (52 ml) at a rate such that the reaction temperature did not exceed 0 0C. Stirring was continued for 2 h after which time the reaction mixture was removed from the ice bath and allowed to stir overnight (12 h) at room temperature. The reaction mixture was diluted with 5 H2O (640 ml) then charcoal (~ 3 g) and Celite (~3 g) were added. The mixture was stirred 10 min and then filtered. To the filtrate was added 2 M NaOH (500 ml) with stirring. The resulting precipitate was filtered under vacuum and the filter cake washed with water (3 x 200 ml). The collected solid was dried overnight under vacuum to give a white powder (12.65 g, 98%). o Recrystallization from i-PrOH gave colorless crystals (12.13 g, 94 %) M.P.149 -152 0C. 1H NMR δ 8.54 (bs, 1 H), 7.83-7.82 (m, 1 H), 7.25 (dd, 1 H, J = 8.24 Hz, J = 1.92 Hz), 7.17 (dd, 1 H, J = 8.79 Hz, J = 0.55 Hz), 7.06 (d, 2.27 Hz), 3.57 (s, 2 H), 2.70 (s, 6 H); 13C NMR δ 134.8, 129.6, 124.8, 124.7, 121.9, 113.1, 112.8, 112.5, 54.4, 45.3; IR (thin film, CHCl3, cm'1) 3429, 3104, 5 2995, 2818, 2589, 1450; FAB MS n-z 253.12 (M+); Anal. Calcd. forC11H13BrN2: C, 52.19; H, 5.18; N, 11.07. Found: C, 52.25; H, 5.24; N, 11.10.

Reference： [1]Current Patent Assignee: DUKE UNIVERSITY - WO2006/102126, 2006, A2 Location in patent: Page/Page column 25

18
[ 830-93-3 ]
[ 64-19-7 ]
C₁₁H₁₁BrN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine; acetic acid In tetrahydrofuran for 0.666667h; Stage #2: With dimethyl sulfate In tetrahydrofuran at 10 - 15℃; for 1h;	2 Under an atmosphere of argon, a solution of 1 (9.00 g, 36.0 mmol) and 17 M acetic acid (0.54 ml, 9.18 mmol) 0 in anhydrous TΗF (50 ml), was added dropwise with stirring over 40 minutes EPO to a solution of dimethyl sulfate (17.5 ml, 180 mmol) and 17 M acetic acid (0.54 ml, 9.18 mmol) in anhydrous THF (20 ml). During the addition, the reaction temperature was kept between 10-15 0C. Stirring was continued for 1 h, after which time a white solid was filtered off under vacuum. The filter cake was washed with Et2O (200 ml) and air dried for 1 h. The collected white powder (13.02 g, 100%) was dissolved with vigorous stirring in water (70 ml) containing KCN (6.94 g, 106 mmol). The solution was then heated on an oil bath at 60-70 0C (internal) for 1 h. After cooling to room temperature, the reaction mixture was extracted with Et2O (2 x 150 ml). The combined organic extracts were washed with saturated aqueous NaHCO3 (100 ml), saturated aqueous NaCl (2 x 100 ml) and dried (Na2SO4). The drying agent was removed by filtration and the filtrate was concentrated under reduced pressure to give a pale solid that was recrystallized from CCl4 to give the desired nitrile as pale micro needles (7.62 g, 90 % from 1). M.P. 100 - 102 0C (Juby and Hudyma, JMed.Chem. 12: 3396-3401 (1969)) 102.5 - 104 0C). 1H NMR 6 8.23 (bs, 1 H), 7.72 - 7.70 (m, 1 H), 7.35 - 7.22 (m, 3 H), 3.79 (s, 2 H); 13C NMR δ 134.8, 127.7, 125.8, 124.0, 120.7, 117.8, 113.5, 113.0, 104.4, 14.3; IR (thin film, CHCl3, cm"1) 3423, 2361, 2253, 1569, 1461; FAB MS m/z 236.1 (MH+); Anal. Calcd. for Ci0H7BrN2: C, 51.09; H, 3.00; N, 11.92. Found: C, 51.07; H, 3.03; N, 11.87.

Reference： [1]Current Patent Assignee: DUKE UNIVERSITY - WO2006/102126, 2006, A2 Location in patent: Page/Page column 25-26

19
[ 1177496-99-9 ]
[ 830-93-3 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: C₁₁H₁₁BrN₂O With n-butyllithium In hexane; toluene at 0 - 5℃; Inert atmosphere; Stage #2: With diisobutylaluminium hydride In hexane; toluene at 0 - 50℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Todd, Robert; Hossain, M. Mahmun [Synthesis, 2009, # 11, p. 1846 - 1850]

20
[ 830-93-3 ]
[ 105-53-3 ]
[ 1206699-21-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With propynoic acid ethyl ester In diethyl ether at 20℃; for 1h; Inert atmosphere;
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 0.75h;	General procedure: To a stirred mixture of S1 (R = H, F, Br, or OMe; 5.20 mmol) and diethyl malonate (4.85 mmol) in Et2O (2.6mL) was added dropwise ethyl propiolate (5.20 mmol) at room temperature. The mixture was stirred for 45 min atthis temperature, followed by quenching with H2O. The whole was extracted with Et2O. The extract was washedsuccessively with H2O and brine, and dried over MgSO4. The filtrate was concentrated under reduced pressure togive an oily residue, which was purified by flash chromatography over silica gel with n-hexane-EtOAc (8:1) togive the corresponding S2 as a pale yellow needle.
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h;

With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h; Schlenk technique; Inert atmosphere;

Reference： [1]Bandini, Marco; Eichholzer, Astrid [Angewandte Chemie - International Edition, 2009, vol. 48, # 50, p. 9533 - 9537]
[2]Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki [Tetrahedron, 2015, vol. 71, # 37, p. 6580 - 6585]
[3]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]
[4]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 23, p. 9672 - 9676]

21
[ 10075-50-0 ]
[ 33797-51-2 ]
[ 830-93-3 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid In methanol at 25℃; for 4h; Inert atmosphere;

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

22
[ 830-93-3 ]
[ 152213-61-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ethanol / 14 h / 25 °C / Inert atmosphere 2: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

23
[ 830-93-3 ]
[ 152213-63-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2101 - 2112

24
[ 830-93-3 ]
[ 152213-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

25
[ 830-93-3 ]
[ 916244-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

26
[ 830-93-3 ]
[ 117235-22-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

27
[ 830-93-3 ]
[ 1361550-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

28
[ 830-93-3 ]
[ 1361550-23-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

29
[ 830-93-3 ]
[ 1361550-25-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

30
[ 830-93-3 ]
[ 1044054-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

31
[ 830-93-3 ]
[ 1361550-28-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

32
[ 830-93-3 ]
2-(5-bromo-1H-indol-3-yl)-N-(2-iodophenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: 2-chloro-1-methyl-pyridinium iodide / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 22 h / Inert atmosphere; Reflux

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

33
[ 830-93-3 ]
[ 1361550-29-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

34
[ 830-93-3 ]
[ 40432-84-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2101 - 2112

35
[ 830-93-3 ]
[ 142273-20-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2101 - 2112

36
[ 830-93-3 ]
[ 142273-23-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: ethanol / 14 h / 25 °C / Inert atmosphere 2.1: water; N,N-dimethyl-formamide / 4 h / 70 °C / Inert atmosphere 3.1: water; potassium hydroxide / methanol / 2 h / 100 °C / Inert atmosphere 3.2: 0 °C / pH 1 / Inert atmosphere 4.1: hydrogenchloride; thionyl chloride; benzotriazol-1-ol / 4 h / 0 - 25 °C / Inert atmosphere 5.1: iodine; silver trifluoromethanesulfonate / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 6.1: 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; caesium carbonate; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

Reference： [1]Soto, Sara; Vaz, Esther; Dell'Aversana, Carmela; Alvarez, Rosana; Altucci, Lucia; De Lera, Angel R. [Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112]

37
[ 830-93-3 ]
[ 813-19-4 ]
[ 1396320-76-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With dichloro bis(acetonitrile) palladium(II); tricyclohexylphosphine In 1,4-dioxane at 110℃; Inert atmosphere;

Reference： [1]Corcoran, Emily B.; Williams, Anna B.; Hanson, Robert N. [Organic Letters, 2012, vol. 14, # 17, p. 4630 - 4633]

38
[ 830-93-3 ]
[ 50824-05-0 ]
C₁₉H₁₉BrF₃N₂O⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane at 25℃;

Reference： [1]Todd, Robert; Huisman, Matthew; Uddin, Nazim; Oehm, Sarah; Hossain, M. Mahmun [Synlett, 2012, vol. 23, # 18, p. 2687 - 2691]

39
[ 830-93-3 ]
[ 109-77-3 ]
gramine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With propynoic acid ethyl ester In dichloromethane at 0 - 20℃; for 24h; Inert atmosphere;

Reference： [1]Dange, Nitin S.; Hong, Bor-Cherng; Lee, Chih-Ching; Lee, Gene-Hsiang [Organic Letters, 2013, vol. 15, # 15, p. 3914 - 3917]

40
[ 830-93-3 ]
C₃₃H₂₉BrN₄ [ No CAS ]
C₃₃H₂₉BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: propynoic acid ethyl ester / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: benzoic acid; (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / dichloromethane / 48 h / 10 °C / Inert atmosphere 3: (+)-CAS / dichloromethane / 24 h / 10 °C / Inert atmosphere

Reference： [1]Dange, Nitin S.; Hong, Bor-Cherng; Lee, Chih-Ching; Lee, Gene-Hsiang [Organic Letters, 2013, vol. 15, # 15, p. 3914 - 3917]

41
[ 830-93-3 ]
gramine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: propynoic acid ethyl ester / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere 2: benzoic acid; (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine / dichloromethane / 48 h / 10 °C / Inert atmosphere

Reference： [1]Dange, Nitin S.; Hong, Bor-Cherng; Lee, Chih-Ching; Lee, Gene-Hsiang [Organic Letters, 2013, vol. 15, # 15, p. 3914 - 3917]

42
[ 830-93-3 ]
O-octadecyl S-(trifluoromethyl)carbonothioate [ No CAS ]
5-bromo-3-(((trifluoromethyl)thio)methyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;

Reference： [1]Li, Shi-Guang; Zard, Samir Z. [Organic Letters, 2013, vol. 15, # 22, p. 5898 - 5901]

43
[ 832114-00-8 ]
[ 830-93-3 ]
[ 1613695-55-8 ]

Yield	Reaction Conditions	Operation in experiment
9%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); sodium hydrogencarbonate In 1,2-dimethoxyethane at 100℃; for 24h; Inert atmosphere;

Reference： [1]Hay, Duncan A.; Fedorov, Oleg; Martin, Sarah; Singleton, Dean C.; Tallant, Cynthia; Wells, Christopher; Picaud, Sarah; Philpott, Martin; Monteiro, Octovia P.; Rogers, Catherine M.; Conway, Stuart J.; Rooney, Timothy P. C.; Tumber, Anthony; Yapp, Clarence; Filippakopoulos, Panagis; Bunnage, Mark E.; Müller, Susanne; Knapp, Stefan; Schofield, Christopher J.; Brennan, Paul E. [Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9308 - 9319]

44
[ 830-93-3 ]
[ 1449676-69-0 ]
C₂₂H₂₂BrFN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; iodobenzene; sodium t-butanolate at 20℃; for 1h; Inert atmosphere; Reflux;

Reference： [1]Roche, Maxime; Bignon, Jérôme; Brion, Jean-Daniel; Hamze, Abdallah; Alami, Mouad [Journal of Organic Chemistry, 2014, vol. 79, # 16, p. 7583 - 7592]

45
[ 830-93-3 ]
[ 877-03-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridinium chlorochromate In N,N-dimethyl-formamide at 100℃; for 0.5h;	General procedure for the oxidation of 4 General procedure: PCC (1.1 mmol) was added to a stirred solution of 4 (1mmol) in DMF (5 mL) at 100 °C (pre-heated oil bath) and the mixture was stirred at 100 °C for 0.5 h.After cooling, the resulting mixture was added to 10% aqueous HCl solution, extracted with AcOEt (100mL), washed with brine, and dried over MgSO4. The solvent was removed, and the residue was purifiedby silica gel column chromatography with CH2Cl2 to give 2.

Reference： [1]Itoh, Tomoki; Abe, Takumi; Nakamura, Shuhei; Ishikura, Minoru [Heterocycles, 2015, vol. 91, # 7, p. 1423 - 1428]

46
[ 830-93-3 ]
[ 1510820-49-1 ]
diethyl 7-bromo-11-methylene-1-tosyl-2,3,10,10a-tetrahydro-1H-2,5a-methanoazepino[2,3-b]indole-4,4(5H)-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: propynoic acid ethyl ester / diethyl ether / 0.75 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 2.2: 2 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 20 °C 5.1: caesium carbonate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 1,4-di(diphenylphosphino)-butane / tetrahydrofuran / 3 h / 60 °C / Inert atmosphere

Reference： [1]Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki [Tetrahedron, 2015, vol. 71, # 37, p. 6580 - 6585]

47
[ 830-93-3 ]
C₂₆H₃₆BrNO₅Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 0.75 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 2.2: 2 h / 0 - 20 °C

Reference： [1]Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki [Tetrahedron, 2015, vol. 71, # 37, p. 6580 - 6585]

48
[ 830-93-3 ]
[ 1318072-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 0.75 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 2.2: 2 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

Reference： [1]Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki [Tetrahedron, 2015, vol. 71, # 37, p. 6580 - 6585]

49
[ 830-93-3 ]
[ 1510820-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: propynoic acid ethyl ester / diethyl ether / 0.75 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 2.2: 2 h / 0 - 20 °C 3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C 4.1: N-chloro-succinimide; triphenylphosphine / dichloromethane / 20 °C

Reference： [1]Iwata, Akira; Inuki, Shinsuke; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki [Tetrahedron, 2015, vol. 71, # 37, p. 6580 - 6585]

50
[ 830-93-3 ]
[ 6287-38-3 ]
C₁₆H₁₀BrCl₂N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28%	With tributylphosphine In acetonitrile at 80℃; for 24h; Inert atmosphere;	1 (1155) The commercially available 5-bromo-3-[(dimethylamino)methyl]indole, bromogramine) (131) (1.02 g, 3.95 mmol, 1 equiv) was dissolved in 10-15 ml acetonitrile. To this was added 3,4-dichlorobenzaldehyde (1.04 g, 5.93 mmol, 1.5 equiv). The flask was flushed with argon and tri-n-butylphosphine was added (1.2 grams (1.48 ml), 5.93 mmol, 1.5 equiv). This mixture was warmed to 80° C. for 24 hours. Cool and concentrate in vacuo (bath temp 30° C.). To the residue was added 50 ml 80/20 hexane:EtOAc and this was passed through a prepared pad of SiO2 in a medium frit buchner funnel and eluted with 80/20 hexane: EtOAc. The cleaned product was isolated and further purified by SiO2 flash chromatography (99/1 hexane: EtOAc) to give 0.4 grams of the desired product (compound 132) (28%). (1156) 1H NMR (DMSO-d6, 400 MHz) δ 11.60 (bs, 1H), d 8.24 (d, J=2 Hz, 1H), d 7.92 (d, J=2 Hz, 1H), d 7.75 (s, 1H), d 7.52-7.62 (m, 3H), d 7.4 (d, 8.8 Hz, 1H), d 7.28 (dd, J=8.8 Hz, J=2 Hz, 1H), d 7.6 (d, J=16.4 Hz, 1H).

Reference： [1]Current Patent Assignee: SYNERECA PHARMACEUTICALS - US2016/168140, 2016, A1 Location in patent: Paragraph 1155; 1156

51
[ 830-93-3 ]
[ 6287-38-3 ]
C₂₁H₂₁BrCl₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tributylphosphine / acetonitrile / 24 h / 80 °C / Inert atmosphere 2.1: sodium hydride / acetonitrile; mineral oil / 0.5 h / 20 °C 2.2: 2 h / 50 °C

Reference： [1]Current Patent Assignee: SYNERECA PHARMACEUTICALS - US2016/168140, 2016, A1

52
[ 830-93-3 ]
[ 33513-42-7 ]
3-((dimethylamino)methyl)-1H-indole-5-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: N-[(5-bromo-1H-indol-3-yl)methyl]-N,N-dimethylamine With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane; mineral oil at -10 - 0℃; for 1h; Stage #3: N,N-dimethyl-formamide In tetrahydrofuran; hexane; mineral oil at 20℃; for 2h;	8.2 2. To a solution of l-(5-bromo-lH-indol-3-yl)-N,N-dimethylmethanamine (2.5 g, 9.88 mmol) in 55 mL of THF, was added sodium hydride (60 wt% dispersion, 475 mg, 11.9 mmol) at 0 °C. After 30 min, the reaction was added 9.4 mL of n-BuLi solution in hexanes (2.5 M) at -10 °C. After 1 hr, DMF (7.7mL) was added and allowed to warm to RT. After 2 hr, the reaction was quenched with water, and extracted with EtOAc (x3). The combined organic extracts were washed with water (x3), dried (MgS04), and concentrated to give 3-((dimethylamino)methyl)- lH-indole-5-carbaldehyde (1.4 g, 70% ). *H NMR (400 MHz, DMSO-i) δ ppm: 11.42 (s, 1H), 9.95 (s, 1H), 8.21 (s, 1H), 7.61 (dd, J=8.4, 1.6 Hz, 1H), 7.48 (d, J= 8.4 Hz, 1H), 7.37 (d, J=2.0 Hz, 1H) 3.56 (s, 2H), 2.14 (s, 6H).

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1 Location in patent: Paragraph 0134

53
[ 830-93-3 ]
(3-((dimethylamino)methyl)-1H-indol-5-yl)(5-methoxy-1H-indol-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C 3.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 1 h / -78 - 0 °C 4.1: manganese(IV) oxide / dichloromethane / 20 °C 5.1: trifluoroacetic acid / dichloromethane / 6 h / 20 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

54
[ 830-93-3 ]
tert-butyl 3-((dimethylamino)methyl)-5-formyl-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

55
[ 830-93-3 ]
tert-butyl 3-((dimethylamino)methyl)-5-(5-methoxy-1-(phenylsulfonyl)-1H-indole-2-carbonyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C 3.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 1 h / -78 - 0 °C 4.1: manganese(IV) oxide / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

56
[ 830-93-3 ]
tert-butyl 3-((dimethylamino)methyl)-5-(hydroxy(5-methoxy-1-(phenylsulfonyl)-1H-indol-2-yl)methyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C 3.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 1 h / -78 - 0 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

57
[ 830-93-3 ]
tert-butyl 3-((dimethylamino)methyl)-5-(hydroxy(5-methoxy-1H-indol-2-yl)methyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C 3.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 1 h / -78 - 0 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

58
[ 830-93-3 ]
tert-butyl 3-((dimethylamino)methyl)-5-(5-methoxy-1H-indole-2-carbonyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C 1.2: 1 h / -10 - 0 °C 1.3: 2 h / 20 °C 2.1: dmap / tetrahydrofuran / 20 °C 3.1: tert.-butyl lithium / tetrahydrofuran; hexane / 1 h / -78 °C 3.2: 1 h / -78 - 0 °C 4.1: manganese(IV) oxide / dichloromethane / 20 °C

Reference： [1]Current Patent Assignee: SRI INTERNATIONAL INC - WO2016/114816, 2016, A1

59
[ 830-93-3 ]
[ 108-59-8 ]
[ 1373115-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h;
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h; Schlenk technique; Inert atmosphere;
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 16h; Inert atmosphere; Schlenk technique;

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]
[2]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 23, p. 9672 - 9676]
[3]Becker, Antonia; Breit, Bernhard; Grugel, Christian P. [Organic Letters, 2021, vol. 23, # 9, p. 3788 - 3792]

60
[ 830-93-3 ]
C₁₆H₁₈BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Schlenk technique; Inert atmosphere

61
[ 830-93-3 ]
6-bromo-2',2'-dimethyl-1-vinyl-1,2,4,9-tetrahydrospiro[carbazole-3,5'-[1,3]dioxane] [ No CAS ]
(S)-6-bromo-2',2'-dimethyl-1-vinyl-1,2,4,9-tetrahydrospiro[carbazole-3,5'-[1,3]dioxane] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 4.1: toluene-4-sulfonic acid / 20 °C 5.1: pyridinium p-toluenesulfonate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

62
[ 830-93-3 ]
diethyl 2-((5-bromo-1H-indol-3-yl)methyl)-2-(buta-2,3-dien-1-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere

63
[ 830-93-3 ]
diisopropyl 2-((5-bromo-1H-indol-3-yl)methyl)-2-(buta-2,3-dien-1-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere

64
[ 830-93-3 ]
di-tert-butyl 2-((5-bromo-1H-indol-3-yl)methyl)-2-(buta-2,3-dien-1-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere

65
[ 830-93-3 ]
5-bromo-3-((5-(buta-2,3-dien-1-yl)-2,2-dimethyl-1,3-dioxan-5-yl)methyl)-1H-indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 4.1: toluene-4-sulfonic acid / 20 °C
	Multi-step reaction with 4 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Schlenk technique; Inert atmosphere 4.1: toluene-4-sulfonic acid / 20 °C / Schlenk technique; Inert atmosphere

66
[ 830-93-3 ]
dimethyl (S)-6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

67
[ 830-93-3 ]
diethyl (S)-6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

68
[ 830-93-3 ]
diisopropyl (S)-6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

69
[ 830-93-3 ]
di-tert-butyl (S)-6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

70
[ 830-93-3 ]
dimethyl 6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

71
[ 830-93-3 ]
diethyl 6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

72
[ 830-93-3 ]
diisopropyl 6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

73
[ 830-93-3 ]
di-tert-butyl 6-bromo-1-vinyl-1,2,4,9-tetrahydro-3H-carbazole-3,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: pyridinium p-toluenesulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

74
[ 830-93-3 ]
6-bromo-2',2'-dimethyl-1-vinyl-1,2,4,9-tetrahydrospiro[carbazole-3,5'-[1,3]dioxane] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C 4.1: toluene-4-sulfonic acid / 20 °C 5.1: pyridinium p-toluenesulfonate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / dichloromethane / 16 h / 40 °C / Inert atmosphere; Schlenk technique; Sealed tube

Reference： [1]Grugel, Christian P.; Breit, Bernhard [Organic Letters, 2019, vol. 21, # 15, p. 5798 - 5802]

75
[ 830-93-3 ]
dimethyl 2-((5-bromo-1H-indol-3-yl)methyl)-2-(buta-2,3-dien-1-yl)malonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C 2.2: 0 - 20 °C
	Multi-step reaction with 2 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere

76
[ 830-93-3 ]
[ 13195-64-7 ]
C₁₈H₂₂BrNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h;
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h; Schlenk technique; Inert atmosphere;

77
[ 830-93-3 ]
[ 541-16-2 ]
C₂₀H₂₆BrNO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h;
	With propynoic acid ethyl ester In diethyl ether at 20℃; for 2h; Schlenk technique; Inert atmosphere;

78
[ 830-93-3 ]
5-bromo-2'',2''-dimethyl-4'-vinyldispiro[indoline-3,3'-cyclopentane-1',5''-[1,3]dioxane] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: propynoic acid ethyl ester / diethyl ether / 2 h / 20 °C / Schlenk technique; Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Schlenk technique; Inert atmosphere 2.2: 0 - 20 °C / Schlenk technique; Inert atmosphere 3.1: lithium aluminium tetrahydride / diethyl ether / 0 - 20 °C / Schlenk technique; Inert atmosphere 4.1: toluene-4-sulfonic acid / 20 °C / Schlenk technique; Inert atmosphere 5.1: chloro(1,5-cyclooctadiene)rhodium(I) dimer; pyridinium p-toluenesulfonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / dichloromethane / 16 h / 40 °C / Schlenk technique; Inert atmosphere; Sealed tube