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Quality Control of Methyl 6-bromo-1H-indole-3-carboxylate Purity: 95% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Methyl 6-bromo-1H-indole-3-carboxylate

CAS No. :	868656-97-7
Formula :	C₁₀H₈BrNO₂
M.W :	254.08
SMILES Code :	COC(=O)C1=CNC2=C1C=CC(Br)=C2
MDL No. :	MFCD09836005
InChI Key :	SKZJYJMYLUQJPG-UHFFFAOYSA-N
Pubchem ID :	11499811

Safety of Methyl 6-bromo-1H-indole-3-carboxylate

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H317
Precautionary Statements:	P280

Application In Synthesis of Methyl 6-bromo-1H-indole-3-carboxylate

* 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 [ 868656-97-7 ]
Downstream synthetic route of [ 868656-97-7 ]

[ 868656-97-7 ] Synthesis Path-Upstream 1~7

1
[ 67-56-1 ]
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 0.0333333 h;	Preparation 39 6-Bromo-lH-indole-3-carboxylic acid methyl esterTo a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M+2).

References: [1] Patent: WO2007/140183, 2007, A1, . Location in patent: Page/Page column 36.

2
[ 67-56-1 ]
[ 17826-04-9 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: at 20℃; for 0.0833333 h; Stage #2: at 20℃; Inert atmosphere	13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite^.(R). and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51percent based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. ¹H NMR (J₆-DMSO, 400 MHz): δ 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)^".

References: [1] Patent: WO2008/157270, 2008, A1, . Location in patent: Page/Page column 102-103.

3
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 20℃; for 0.0333333 h;	Intermediate Preparation 40; 6-Bromo-lH-indole-3-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, about 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is re-dissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M + 2).
100%	at 20℃; for 0.0333333 h;	Preparation 13; -Bromo-lH-indole-S-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, ca 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100percent). ES/MS m/e 256.0 (M + 2).

References: [1] Patent: WO2009/12125, 2009, A1, . Location in patent: Page/Page column 36.
[2] Patent: WO2007/140174, 2007, A2, . Location in patent: Page/Page column 24.
[3] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867.

4
[ 67-56-1 ]
[ 101774-27-0 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride In water for 2 h; Inert atmosphere; Reflux	To a stirred solution of VII-3 (0.86 g, 3.6 mmol) in MeOH (30 mL) was added aq. HCl (0.5 mL) under nitrogen. After the addition, the solution was heated to reflux under nitrogen for 2 hours. The solvent was removed by reduced pressure and the residue was added sat. NaHCO₃to adjust to pH=9 and the solution was extracted with DCM, the combine organic layer was dried and concentrated in vacuum to afford VII-4 (0.71 g, 78percent) as a yellow solid which was used for next step directly.
72%	at 65℃;	Step 9; -Bromo-lH-indole-S-carboxylic acid methyl ester; Acetyl chloride (29,43 g, 374 mmol) is added slowly at room temperature to a solution of 6-bromo-indole-3-carboxylic acid (45 g, 187.46 mmol) in 50OmL of methanol and the resulting solution is stirred at 65⁰C overnight. The reaction is cooled to room temperature. A white precipitates appears when cooling. After stirring 2h at room temperature, the solid is filtered off and dried under vacuum. 34.4g (72percent) of the title compound is obtained as a light brown solid. MS (m/e): 254 (M+ 1)

References: [1] Patent: US2014/200215, 2014, A1, . Location in patent: Paragraph 0978; 0981.
[2] Patent: WO2009/12125, 2009, A1, . Location in patent: Page/Page column 61.
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9768 - 9772.

5
[ 52415-29-9 ]
[ 868656-97-7 ]

References: [1] Patent: US2014/200215, 2014, A1, .
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867.
[3] Patent: WO2008/157270, 2008, A1, .

6
[ 79878-02-7 ]
[ 868656-97-7 ]

References: [1] Patent: US2014/200215, 2014, A1, .
[2] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 8, p. 863 - 867.

7
[ 771-50-6 ]
[ 868656-97-7 ]

References: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 24, p. 9768 - 9772.

[ 868656-97-7 ] Synthesis Path-Downstream 1~42

1
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol; hexane; at 20℃; for 0.0333333h;Product distribution / selectivity;	Intermediate Preparation 40; 6-Bromo-lH-indole-3-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, about 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is re-dissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M + 2).
100%	In methanol; hexanes; at 20℃; for 0.0333333h;	Preparation 13; -Bromo-lH-indole-S-carboxylic acid methyl ester; To a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, ca 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure. This process is repeated several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M + 2).

References: [1]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 36.
[2]Patent: WO2007/140174,2007,A2 .Location in patent: Page/Page column 24.
[3]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

2
[ 67-56-1 ]
[ 101774-27-0 ]
[ 18107-18-1 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	In hexanes; at 20℃; for 0.0333333h;	Preparation 39 6-Bromo-lH-indole-3-carboxylic acid methyl esterTo a solution of 6-bromoindole-3-carboxylic acid (960 mg, 4.00 mmol) in methanol (9.5 mL) is added (trimethylsilyl)diazomethane (2.0 M solution in hexanes, approximately 9 mL) over two minutes at room temperature. The yellow mixture is concentrated under reduced pressure. The residue is redissolved in methanol and concentrated under reduced pressure several times to give the title compound as a solid (100%). ES/MS m/e 256.0 (M+2).

References: [1]Patent: WO2007/140183,2007,A1 .Location in patent: Page/Page column 36.

3
[ 868656-97-7 ]
[ 946427-03-8 ]
6-(4-hydroxy-2-methyl-phenyl)-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; N,N-dimethyl-formamide; at 100℃; for 60h;	Preparation 40 6-(4-Hydroxy-2-methyl-phenyl)-lH-indole-3-carboxylic acid methyl esterA mixture of 3-methyl-4-(4,4,5,5-tetramethyl-[l,3,2]dioxaborolan-2-yl)-phenol (213 mg, 0.910 mmol), -bromo-lH-indole-S-carboxylic acid methyl ester (193 mg, 0.759 mmol), tetrakis(triphenylphosphine)palladium(0) (57 mg, 0.046 mmol), DMF (2.7 mL), ethanol (1.34 mL) and 2M aqueous potassium carbonate (1.34 mL) is heated to 100 0C for 60 hours. The reaction is cooled to room temperature, diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ethyl acetate. The combined organic layers are dried over anhydrous magnesium sulfate and concentrated. <n="38"/>The residue is purified with flash chromatography eluting with 25to 40 % ethyl acetate/heptane to give the title compound (134 mg, 63%). ES/MS m/e 280.3 (M-I).

References: [1]Patent: WO2007/140183,2007,A1 .Location in patent: Page/Page column 36-37.

5
[ 868656-97-7 ]
[ 74-88-4 ]
6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 2h;	Preparation 12 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl esterTo a room temperature mixture of 5-bromo-lH-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) and DMF is added iodomethane (30 muL, 0.47 mmol). After 1.5 hours, additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M+2).
99%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;Product distribution / selectivity;	Intermediate Preparation 41; 6-Bromo-l -methyl- IH- indole-3-carboxylic acid methyl ester; To a mixture of 6-bromo- leta-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) in DMF is added iodomethane (30 muL, 0.47 mmol). The reaction mixture is stirred for 1.5 h. Additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give the title compound (105 mg, 99%). ES/MS m/e 270.0 (M + 2).
99%	With potassium carbonate; In N,N-dimethyl-formamide; for 2h;	Preparation 14; 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl ester; To a mixture of 5-bromo-lH-indole-3-carboxylic acid methyl ester (100 mg, 0.394 mmol), potassium carbonate (163 mg, 1.18 mmol) in DMF is added iodomethane (30 muL, 0.47 mmol). The reaction mixture is stirred for 1.5 hours. Additional iodomethane (10 muL) is added and the reaction is stirred for 30 minutes. The reaction mixture is diluted with dichloromethane and filtered. The filtrate is concentrated under high vacuum, diluted with ethyl acetate, and concentrated to give 105 mg (99%) of the title compound. ES/MS m/e 270.0 (M + 2).

88%	With potassium carbonate; In acetonitrile; at 20℃; for 72h;Product distribution / selectivity;	Step 10; 6-Bromo-l -methyl- lH-indole-3-carboxylic acid methyl ester; To a mixture of 25g (98.39 mmol) of 6-bromo-lH-indole-3-carboxylic acid methyl ester and 27.2Og (196 mmol) of potassium carbonate in 30OmL of acetonitrile is added at room temperature Methyl Iodide (20.95g, 147.6 mmol). The reaction mixture is stirred at room temperature for 3 days. The solvent is evaporated, 500 ml of water is <n="63"/>added, and the organic layer is extracted with (3X300 ml) ethyl acetate. The organics are combined, dried over magnesium sulfate and evaporated. The crude is purified by silica gel chromatography eluting with hex/EtOAc 8:2. The title compound (23.3g (88%)) is obtained as a brown solid. MS (m/e): 268 (M+ 1).
	With potassium carbonate; In N,N-dimethyl-formamide; at 25℃; for 6h;	4-3 (400 mg, 1.57 mmol) and potassium carbonate (653 mg, 4.7 mmol) were dissolved in N,N-dimethylformamide (5 mL), and iodomethane (2.9 g, 20.4 mmol, 1.27 mL) was added. The reaction mixture was stirred at 25 C for 6 hours. Dichloromethane (20 ml) was added to the reaction mixture, and then filtered. The filtrate was concentrated to obtain a residue, to which petroleum ether/ethyl acetate (10/1, 10 mL) was added, and filtered. The obtained solid was dried under vacuum, to give the target compound 4-4 without purification. 1H NMR (400MHz, CHLOROFORM-d) delta 8.02 (d, J = 8.5 Hz, 1H), 7.73 (s, 1H), 7.50 (d, J = 1.3 Hz, 1H), 7.37 (dd, J = 1.8, 8.5 Hz, 1H), 3.93 - 3.87 (m, 3H), 3.84 - 3.75 (m, 3H).

References: [1]Patent: WO2007/92751,2007,A2 .Location in patent: Page/Page column 16.
[2]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 37.
[3]Patent: WO2007/140174,2007,A2 .Location in patent: Page/Page column 24.
[4]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 61-62.
[5]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772.
[6]Patent: EP3632910,2020,A1 .Location in patent: Paragraph 0185.

6
[ 868656-97-7 ]
[ 18107-18-1 ]
6-bromo-1-(2-dimethylamino-ethyl)-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%		Preparation 14 6-Bromo-l-(2-dimethylamino-ethyl)-lH-indole-3-carboxylic acid methyl esterA mixture of -bromo-lH-indole-S-carboxylic acid methyl ester (500 mg, 1.97 mmol), sodium hydride (60% in mineral oil, 748 mg, 31.2 mmol), sodium iodide (295 mg, 1.96 mmol), 2- dimethylaminoethyl chloride hydrochloride (341 mg, 2.37 mmol) and DMF (60 mL) is heated at 100 0C for <n="18"/>8 hours. The reaction mixture is cooled, filtered, and the solids are washed with water and air dried. The solids are dissolved in MeOH (200 mL) and (trimethylsilyl)diazomethane (2.0 M solution in hexanes, 20 mL) is added over several minutes. The reaction mixture is stirred for one hour and concentrated under reduced pressure. The residue is partitioned between water and ethyl acetate. The ethyl acetate layer is separated and dried over MgSO4. The crude product is purified via radial chromatography using 2.5% MeOH/CH2Cl2 to afford the title compound (195 mg, 30%). ES/MS m/e 327.0 (M+2).

References: [1]Patent: WO2007/92751,2007,A2 .Location in patent: Page/Page column 16-17.

7
[ 868656-97-7 ]
[ 616-38-6 ]
6-bromo-1-methyl-1H-indole-3-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate; In N,N-dimethyl-formamide; at 130℃;Product distribution / selectivity;	Alternate procedure: Add dimethyl carbonate (1.3 L, 12.4 mol) to a mixture of 6- bromo-lH-indole-3-carboxylic acid methyl ester (1.3 kg, 5.1 mol) and potassium carbonate (1.41 kg, 10.2 mol) in DMF (6.0 L) at room temperature. Heat the mixture to 130 0C and stir overnight. Cool the reaction mixture to ~3 0C and add ice-cold water (6 L). Filter the resulting solid, wash with methanol (2 L) and dry in a vacuum oven to afford 1.1 kg (82%) of the title compound.

References: [1]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 62.

8
[ 67-56-1 ]
[ 101774-27-0 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With hydrogenchloride; In water; for 2h;Inert atmosphere; Reflux;	To a stirred solution of VII-3 (0.86 g, 3.6 mmol) in MeOH (30 mL) was added aq. HCl (0.5 mL) under nitrogen. After the addition, the solution was heated to reflux under nitrogen for 2 hours. The solvent was removed by reduced pressure and the residue was added sat. NaHCO3 to adjust to pH=9 and the solution was extracted with DCM, the combine organic layer was dried and concentrated in vacuum to afford VII-4 (0.71 g, 78%) as a yellow solid which was used for next step directly.
72%	With acetyl chloride; at 65℃;Product distribution / selectivity;	Step 9; -Bromo-lH-indole-S-carboxylic acid methyl ester; Acetyl chloride (29,43 g, 374 mmol) is added slowly at room temperature to a solution of 6-bromo-indole-3-carboxylic acid (45 g, 187.46 mmol) in 50OmL of methanol and the resulting solution is stirred at 650C overnight. The reaction is cooled to room temperature. A white precipitates appears when cooling. After stirring 2h at room temperature, the solid is filtered off and dried under vacuum. 34.4g (72%) of the title compound is obtained as a light brown solid. MS (m/e): 254 (M+ 1)
	With sulfuric acid; at 60℃; for 24h;	4-2 (8.0 g, 33.3 mmol) was dissolved in methanol (20 mL), and concentrated sulfuric acid (32.7 mg, 333.3 mumol, 18 muL, two drops) was added. The reaction mixture was stirred at 60 C for 24 hours, concentrated to remove the solvent. The residue was purified by column chromatography to give the target compound 4-3. 1H NMR (400MHz, CHLOROFORM-d) delta 8.60 (br. s., 1H), 8.05 (d, J = 8.5 Hz, 1H), 7.90 (d, J = 3.0 Hz, 1H), 7.63 - 7.56 (m, 1H), 7.43 - 7.35 (m, 1H), 3.98 - 3.85 (m, 3H).

References: [1]Patent: US2014/200215,2014,A1 .Location in patent: Paragraph 0978; 0981.
[2]Patent: WO2009/12125,2009,A1 .Location in patent: Page/Page column 61.
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772.
[4]Patent: EP3632910,2020,A1 .Location in patent: Paragraph 0184.

9
[ 52415-29-9 ]
[ 868656-97-7 ]

References: [1]Patent: US2014/200215,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.
[3]Patent: WO2008/157270,2008,A1 .

10
[ 868656-97-7 ]
[ 351019-18-6 ]
[ 1093631-88-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; for 15h;Inert atmosphere; Reflux;	13c) Methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylateMethyl 6-bromo-lH-indole-3-carboxylate (0.63 g, 2.48 mmol), 2- fluoropyridyl-5-boronic acid (0.435 g, 3.09 mmol), tetrakistriphenylphosphine palladium (0) (0.14 g, 0.012 mmol), 2 M sodium carbonate (5 mL, 10 mmol), and 1,2- dimethoxyethane (20 mL) were combined and heated at reflux with stirring under a nitrogen atmosphere for 15 hours. The reaction mixture was allowed to cool at room temperature and partitioned between water and ethyl acetate. The organic phase was separated, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as a yellow solid. The crude product was purified by flash chromatography over silica gel with a dichloromethane methanol gradient (100:0 to 97:3) to give 0.606 g of methyl 6-(6-fluoro-3-pyridinyl)-lH-indole-3-carboxylate as a yellow solid. 1H NMR indicates that a minor impurity is present. The compound was used without further purification. 1H NMR (J6-DMSO, 400 MHz): delta 12.09 (br s, IH), 8.54 (d, J = 2 Hz, IH), 8.28 (dt, J = 8, 3 Hz, IH), 8.13 (d, J = 3 Hz, IH), 8.06 (d, J = 8 Hz, IH), 7.73 (s, IH), 7.51 (dd, J = 8, 2 Hz, IH), 7.27 (dd, J = 9, 3 Hz, IH), 3.80 (s, 3H). ES-LCMS m/z 269 (M - H)".

References: [1]Patent: WO2008/157270,2008,A1 .Location in patent: Page/Page column 103.

11
[ 868656-97-7 ]
[ 1093631-89-0 ]

References: [1]Patent: WO2008/157270,2008,A1 .

12
[ 868656-97-7 ]
[ 1093631-54-9 ]

References: [1]Patent: WO2008/157270,2008,A1 .

13
[ 67-56-1 ]
[ 17826-04-9 ]
[ 868656-97-7 ]

Yield	Reaction Conditions	Operation in experiment
51%		13b) Methyl -bromo-lH-indole-S-carboxylateTo a stirred solution of -bromo-lH-indole-S-carbaldehyde (1.6 g, 7.1 mmol) in methanol (70 mL) was added sodium cyanide (1.7 g, 34.7 mmol) at room temperature. The reaction mixture was stirred for five minutes and then manganese (IV) oxide (7.4 g, 85.1 mmol) was added portionwise over a period of 2.5 hours. The reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. To the reaction mixture was added dichloromethane (75 mL). The reaction mixture was filtered through a pad of Celite and the pad was washed with <n="104"/>dichloromethane. The cloudy filtrate was concentrated in vacuo and the residue was partitioned between water and ethyl acetate. The organic phase was separated, washed with water, dried over magnesium sulfate, filtered, and the filtrate was concentrated to give the crude product as an off-white solid. The crude product was purified by flash chromatography over silica gel with a hexanes: ethyl acetate gradient (100:0 to 0: 100) to give 0.636 g (51% based on recovered starting material) of methyl 6-bromo-lH-indole-3-carboxylate as an off-white solid. 1H NMR (J6-DMSO, 400 MHz): delta 12.02 (br s, IH), 8.09 (s, IH), 7.90 (d, J = 9 Hz, IH), 7.65 (d, J = 2 Hz, IH), 7.31 (dd, J = 9, 2 Hz, IH), 3.78 (s, 3H). ES-LCMS m/z 252 (M - H)".

References: [1]Patent: WO2008/157270,2008,A1 .Location in patent: Page/Page column 102-103.

14
[ 79878-02-7 ]
[ 868656-97-7 ]

References: [1]Patent: US2014/200215,2014,A1 .
[2]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.
[3]Patent: EP3632910,2020,A1 .

15
[ 868656-97-7 ]
[ 177407-39-5 ]
C₁₅H₁₅NO₂ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

16
[ 868656-97-7 ]
[ 1615201-61-0 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

17
[ 868656-97-7 ]
C₁₃H₁₁NO₃ [ No CAS ]
C₉H₇NO₄ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

18
[ 868656-97-7 ]
[ 1615201-63-2 ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

19
[ 868656-97-7 ]
C₁₄H₁₃NO₂ [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

20
[ 868656-97-7 ]
C₁₄H₁₅NO [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2014,vol. 5,p. 863 - 867.

21
[ 868656-97-7 ]
[ 16133-25-8 ]
methyl 6-bromo-1-(pyridin-3-ylsulfonyl)-1H-indol-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		Step 1: Preparation of methyl6-bromo-1-(pyridin-3-ylsulfonyl)-1H-indol-3-carboxylate Methyl 6-bromo-1H-indol-3-carboxylate (200 mg, 0.8 mmol) was dissolved in 2 ml of tetrahydrofuran solution, cooled to 0C, and dropwisely added with sodium hydride(60% in oil) (44 mg, 1.1 mmol). The reaction mixture was stirred at ooc for 30minutes, added with pyridin-3-sulfonyl chloride (232 mg, 1.1 mmol) prepared in Step1 of Example 1, and stirred at room temperature for 12 hours. The resulting reaction mixture was added with water and extracted with ethyl acetate. The resulting separated organic layer was washed with saturated brine, dried on anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1 : 2 (v/v)) to obtain 250 mg of a title compound (yield: 80%).[2151] 1H NMR (300 MHz, CDCb): 8.88 (d, 1H), 8.57 (s, 1H), 8.27 (dd, 1H), 8.03 (dd, 1H),7.54 (d, 1H), 7.49 (d, 1H), 7.25 (s, 1H), 7.21 (d, 1H), 3.97 (s, 9H)

References: [1]Patent: WO2015/50412,2015,A1 .Location in patent: Paragraph 2146; 2147; 2149; 2150; 2151.

22
[ 771-50-6 ]
[ 868656-97-7 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772.

23
[ 868656-97-7 ]
[ 1103500-20-4 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772.

24
[ 868656-97-7 ]
[ 1103500-82-8 ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 9768 - 9772.

25
[ 868656-97-7 ]
[ 98-09-9 ]
methyl 6-bromo-1-(phenylsulfonyl)-1H-indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		Synthesis of methyl 6-bromo-l-(phenylsulfonyl)-lH-indole-3-carboxylate (205); To a stirred solution of methyl carboxylate 212 (2.97 g, 1 1.7 mmol) in THF (50 ml) at 0C was added NaH (60% in oil, 560 mg, 14.0 mmol) gradually. After stirring at room temperature for 10 minutes, benzenesulphonyl chloride (1.80 ml, 14.1 mmol) was added and the mixture was further stirred at rt for 3h. The reaction was quenched with H20 and extracted with EtOAc (2 x 50 ml). The combined organic phases were washed with brine, dried over anhydrous Na2S04, filtered and concentrated in vacuo. The crude product was purified by automated flash chromatography to give compound 205 as a tan solid (4.24g, 92%). NMR (400 MHz, CDC13) delta 8.61 (d, J= 1.7 Hz, 1 H), 7.98 - 7.94 (m, 2H), 7.92 (d, J = 8.6 Hz, 1H), 7.67 - 7.61 (m, 1H), 7.51 (t, J = 7.9 Hz, 2H), 7.44 (dd, J = 8.7, 1.7 Hz, 1H), 3.95 (s, 3H). Mass calculated for (C16H12BrN04S+H)+ 394.0, found

References: [1]Patent: WO2016/4513,2016,A1 .Location in patent: Paragraph 00555; 00556.

26
[ 868656-97-7 ]
6-bromo-3-(methoxycarbonyl)-1H-indole-2-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

27
[ 868656-97-7 ]
methyl 6-bromo-2-((4-chlorophenyl)carbamoyl)-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

28
[ 868656-97-7 ]
6-bromo-2-((4-chlorophenyl)carbamoyl)-1H-indole-3-carboxylic acid [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

29
[ 868656-97-7 ]
methyl 6-bromo-2-((5-chloropyridin-2-yl)carbamoyl)-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

30
[ 868656-97-7 ]
methyl 6-bromo-2-iodo-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

31
[ 868656-97-7 ]
methyl 6-bromo-2-((triisopropylsilyl)ethynyl)-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

32
[ 868656-97-7 ]
methyl 6-bromo-2-ethynyl-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

33
[ 868656-97-7 ]
methyl 6-bromo-2-((5-chloro-1H-indol-2-yl)ethynyl)-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

34
[ 868656-97-7 ]
C₂₀H₁₉NO₃ [ No CAS ]
C₂₀H₁₉NO₃ [ No CAS ]

References: [1]Chinese Journal of Chemistry,2017,vol. 35,p. 1512 - 1516.

35
[ 868656-97-7 ]
C₁₄H₁₄BrNO₃ [ No CAS ]

References: [1]Chinese Journal of Chemistry,2017,vol. 35,p. 1512 - 1516.

36
[ 868656-97-7 ]
[ 513-42-8 ]
C₁₄H₁₄BrNO₃ [ No CAS ]

References: [1]Chinese Journal of Chemistry,2017,vol. 35,p. 1512 - 1516.

37
[ 868656-97-7 ]
[ 98-09-9 ]
methyl 6-bromo-2-iodo-1-(phenylsulfonyl)-1H-indole-3-carboxylate [ No CAS ]

References: [1]Patent: WO2016/4513,2016,A1 .

38
[ 868656-97-7 ]
[ 73183-34-3 ]
methyl 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; at 95℃; for 17h;Inert atmosphere;	To a solution of <strong>[868656-97-7]methyl 6-bromo-1H-indole-3-carboxylate</strong> (500 mg, 1.97 mmol) in anh. DMF (10 mL) are added atRT 4,4,4,4,5,5,5,5-octamethyl-2,2-bi(1,3,2-dioxaborolane) (505 mg, 1.97 mmol), potassium acetate (773 mg,7.87 mmol) and Pd(dppf)C12 (160 mg, 0.21 mmol). The RM is heated to 95C, under nitrogen, for 17h. The RM is then allowed to cool to RT and is filtered through a pad of celite, washing with Et20. The filtrate is washed with water and the aqueous layer is extracted twice with Et20. The combined organic layers are then washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by FC (from heptane toheptane/EtOAc = 7/3) affords methyl 6-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-indole-3-carboxylate as a colorless solid (186 mg, 31%). LC-MS B: tR = 0.96 mm; [M+H] = 302.25.

References: [1]Patent: WO2018/210988,2018,A1 .Location in patent: Page/Page column 169.

39
[ 868656-97-7 ]
[ 76513-69-4 ]
methyl 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.36 g	With sodium hydride; In tetrahydrofuran; water; at 20 - 25℃;	Sodium hydride (48.0 mg, 1.2 mmol) was added to a room temp solution of <strong>[868656-97-7]methyl 6-bromo-1H-indole-3-carboxylate</strong> (0.25 g, 1.0 mmol) in THF (50 mL). After stirring for 15 minutes, SEM-C1 (0.21 mL, 1.2 mmol) was added and the resulting suspension was stirred at 25C. overnight. Water (50 mL) was added to the reaction mixture giving a sticky precipitate. The solvent was decanted and the residue was purified by flash chromatography on SiO2 (0-30% EtOAc/hexanes, Isco 24 g column) to yield methyl 6-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indole-3-carboxylate (0.36 g, 0.83 mmol) as a gum. MS (ESI) m/z: 384.0 [M+H]+; 1H NMR (500 MHz, CDCl3) delta 8.06 (d, J=8.53 Hz, 1H), 7.86 (s, 1H), 7.72 (d, J=1.65 Hz, 1H), 7.43 (dd, J=1.65, 8.53 Hz, 1H), 5.48 (s, 2H), 4.80 (s, 1H), 3.94 (s, 3H), 1.29 (br t, J=7.15 Hz, 3H), -0.23-0.22 (m, 11H).

References: [1]Patent: US2019/127362,2019,A1 .Location in patent: Paragraph 0739-0740.

40
[ 868656-97-7 ]
methyl (1S,2S)-6-bromo-1-((S)-4-isopropyl-2-oxooxazolidine-3-carbonyl)-2-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate [ No CAS ]

References: [1]Chemical Communications,2019,vol. 55,p. 11303 - 11306.

41
[ 868656-97-7 ]
[ 4206-67-1 ]
methyl 6-bromo-1-[(trimethylsilyl)methyl]-1H-indole-3-carboxylate [ No CAS ]

References: [1]Chemical Communications,2019,vol. 55,p. 11303 - 11306.

42
[ 868656-97-7 ]
C₃₃H₂₇Cl₂N₃O₅ [ No CAS ]

References: [1]Patent: EP3632910,2020,A1 .

Historical Records

Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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CAS No.: 868656-97-7

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CAS No.: 868656-97-7

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Product Details of Methyl 6-bromo-1H-indole-3-carboxylate

Safety of Methyl 6-bromo-1H-indole-3-carboxylate

Application In Synthesis of Methyl 6-bromo-1H-indole-3-carboxylate

[ 868656-97-7 ] Synthesis Path-Upstream 1~7

[ 868656-97-7 ] Synthesis Path-Downstream 1~42

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