1211596-82-5|4-Bromo-1H-indole-7-carboxamide| Ambeed

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Quality Control of [ 1211596-82-5 ] Purity: 95% SDS Specification

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NMR

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CNMR

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Product Details of [ 1211596-82-5 ]

CAS No. :	1211596-82-5
Formula :	C₉H₇BrN₂O
M.W :	239.07
SMILES Code :	NC(=O)C1=CC=C(Br)C2=C1NC=C2
MDL No. :	MFCD12547331
InChI Key :	SRGYDNIXPOHONC-UHFFFAOYSA-N
Pubchem ID :	49757996

Safety of [ 1211596-82-5 ]

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

Application In Synthesis of [ 1211596-82-5 ]

* 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.

Downstream synthetic route of [ 1211596-82-5 ]

[ 1211596-82-5 ] Synthesis Path-Downstream 1~33

1
[ 3460-18-2 ]
[ 1211596-82-5 ]

References: [1]Patent: WO2011/159857,2011,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3080 - 3084.

2
[ 1211596-82-5 ]
[ 68-12-2 ]
[ 1352838-12-0 ]

Yield	Reaction Conditions	Operation in experiment
65%		Example 52; 3-(Hydroxymethyl)-9-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-5H-pyrido[4,3- -6-carboxamide; 1. 4-Bromo-3-formyl-1H-indo -7-carbonitrile; A solution of DMF (8.42 mL, 109 mmol) in CH2C12(105 mL) stirred on a salt- ice bath was treated dropwise with phosphorus oxychloride (2.57 mL, 27.6 mmol). After 15 min, <strong>[1211596-82-5]4-bromo-1H-indole-7-carboxamide</strong> (2 g, 8.37 mmol) was added in one portion while maintaining the temperature below -10 C. After addition, the mixture was stirred at room temperature overnight. After 16 h, ice was added, followed by aHC03 and 1 M aqueous NaOH added in portions to make the mixture basic. The mixture was extracted with dichloromethane (3 times), and the combined organic phases were washed with brine, dried and concentrated. The residue was subjected to column chromatography on silica gel (80g), eluting with a gradient from 100% CH2C12 to 15% Methanol- 85%CH2C12, to provide the desired product as a pale solid (1.36 g, 65% yield). LCMS (M+H)+ m/z 248.9, 250.9.

References: [1]Patent: WO2011/159857,2011,A1 .Location in patent: Page/Page column 210-211.

3
[ 50-00-0 ]
[ 1211596-82-5 ]
[ 124-40-3 ]
[ 1352837-86-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 49; 3-(Hydroxymethyl)-5-(2-methyl-3-(4-oxoquinazolin-3(4H)-yl)phenyl)-9H-pyrido[3,4- b]indole-8-carboxamide; 4-Bromo-3 -((dimethylamino)methyl)- 1 H-indole-7-carboxamide; Acetic acid (1.15 mL, 20.08 mmol) was added to a suspension of 4-bromo- 1H-indole-7-carboxamide (3 g, 12.55 mmol), paraformaldehyde (0.603 g, 20.08 mmol) and dimethylamine (2 M in methanol, 10 mL, 20.08 mmol) in ethanol (50 mL). The mixture was heated to 80 C. After 2 h, the ethanol was removed under vacuum. The residue was partitioned between NaHCC (aq) and EtOAc. The organic phase was washed with brine (15 mL), dried and concentrated to afford the crude desired product as a light brown solid (4.08g). LCMS (M+H)+ m/z 295.8, 297.8.

References: [1]Patent: WO2011/159857,2011,A1 .Location in patent: Page/Page column 204-205.

4
[ 126811-31-2 ]
[ 1211596-82-5 ]

References: [1]Patent: WO2011/159857,2011,A1 .
[2]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 3080 - 3084.

5
[ 73430-27-0 ]
[ 1211596-82-5 ]
(Z)-4-bromo-3-(2-nitrovinyl)-1H-indole-7-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%		4. 4-Bromo-3-(2-nitrovinyl)-1H-indole-7-carboxamide; A dark red-brown solution of <strong>[1211596-82-5]4-bromo-1H-indole-7-carboxamide</strong> (0.79g, 3.30 mmol) and (E)-N,N-dimethyl-2-nitroethenamine (0.422 g, 3.63 mmol) in TFA (9.44 mL) was stirred at room temperature overnight. After 16 h, LCMS indicated residual starting materials in addition to desired product. Additional (E)-N,N-dimethyl-2-nitroethenamine (77 mg) was added and the mixture was stirred at room temperature for 6 h. The mixture was partitioned between 1 M NaOH (pH was adjusted to ca. 4) and EtOAc. The organic phase was washed with NaHCO3 (aq) and brine, dried and concentrated to afford a bright orange-red solid. The crude product was suspended in EtOAc and the desired product was collected by filtration, washed with EtOAc and air dried to provide a solid (0.89 g, 87% yield). LCMS (M+H)+ m/z 309.7, 311.7.

References: [1]Patent: WO2011/159857,2011,A1 .Location in patent: Page/Page column 202.

6
[ 1211594-25-0 ]
[ 1211596-82-5 ]

Yield	Reaction Conditions	Operation in experiment
97%		A solution of 4-bromo-1H-indole-7-carboxylic acid (5.5 g, 22.91 mmol) EDC (6.59 g, 34.4 mmol) and HOBt (5.26 g, 34.4 mmol) in THF (150 mL) and DCM (180 mL) was stirred at rt for 1 h. The mixture was then bubbled with NH3 gas for about 15 mm and the resulting mixture was stirred at rt overnight. The mixture was diluted by addition of water and extracted with DCM. The organic phase was washed with brine, dried and concentrated to give a residue, which was suspended in ether and filtered to provide 4-bromo-]H-indole-7-carboxamide (5.3 g, 97%): ?H NMR (DMSO-d6) 3 11.40 (br, 1H), 8.08 (br, 1H), 7.29-7.57 (d, J = 7.6 Hz, 1H), 7.43-7.42 (m, 2H), 7.28-7.26 (d, J = 7.6 Hz, 1H), 6.43-6.42 (m, 1H).
		3. 4-Bromo- 1 H-indole-7-carboxamide; A mixture of 4-bromo-1H-indole-7-carboxylic acid (10.04 g, 75% purity, 31.2 mmol), EDC (8.96 g, 46.7 mmol), and 1-hydroxybenzotriazole hydrate (7.16 g, 46.7 mmol) in THF (198 mL) and CH2CI2 (247 mL) was stirred at room temperature for 1 h. The mixture was then bubbled with NH3 gas for 15 min and stirred at room temperature for 4 h. LCMS showed residual starting material, so aqueous ammonium hydroxide (4.85 mL, 125 mmol) was added and the mixture was stirred at room temperature overnight. After 20 h, the mixture was concentrated and partitioned between NaHCO3 (aq) and EtOAc. The organic phase was washed with brine, dried and concentrated. The residue was suspended in EtOAc and the solid was collected by filtration and air-dried to provide the desired product. The filtrates were subjected to column chromatography on silica gel (40g), eluting with EtOAc -hexane (gradient from 20:80 to 50:50) to provide additional desired product for a total of 4.86 g (65% yield) over two steps. LCMS (M-H)-: 237.2, 239.2.

References: [1]Patent: WO2014/210255,2014,A1 .Location in patent: Page/Page column 101.
[2]Patent: WO2011/159857,2011,A1 .Location in patent: Page/Page column 201.

7
[ 1211596-82-5 ]
[ 1352837-76-3 ]