374537-99-2|5-Bromo-1H-indol-7-amine| Ambeed

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Quality Control of [ 374537-99-2 ] Purity: 96% SDS Specification

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Product Details of [ 374537-99-2 ]

CAS No. :	374537-99-2
Formula :	C₈H₇BrN₂
M.W :	211.06
SMILES Code :	NC1=CC(Br)=CC2=C1NC=C2
MDL No. :	MFCD02093961
InChI Key :	ZRTCJQGCGWZTAG-UHFFFAOYSA-N
Pubchem ID :	7010313

Safety of [ 374537-99-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 374537-99-2 ]

* 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 [ 374537-99-2 ]

[ 374537-99-2 ] Synthesis Path-Downstream 1~7

1
[ 374537-99-2 ]
[ 4023-34-1 ]
[ 1610801-24-5 ]

Yield	Reaction Conditions	Operation in experiment
76%	With triethylamine; In dichloromethane; for 2.0h;Cooling with ice;	N-(5-Bromo-1H-indol-7-yl)cyclopropanecarboxamide (23A) A solution of cyclopropanecarbonyl chloride (0.54 g, 5.21 mmol) in DCM (10 mL) was added dropwise to an ice-cold solution of <strong>[374537-99-2]5-bromo-1H-indol-7-amine</strong> (1.0 g, 4.74 mmol) and triethylamine (0.991 mL, 7.11 mmol) in DCM (20 mL), and the mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. Separated organic layer was dried over sodium sulphate and filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography using 20% ethyl acetate in hexanes to afford the title compound (1.1 g, 76%) as a red solid. 1H NMR (300 MHz, DMSO-d6): δ 11.0 (s, 1H), 10.08 (s, 1H), 7.72 (s, 1H), 7.48 (s, 1H), 7.41 (t, J=3.0 Hz, 1H), 6.43 (t, J=2.4 Hz, 1H), 1.90-1.86 (m, 1H), 0.88-0.82 (m, 4H). ESI-MS m/z=279 (M+H)+.
76%	With triethylamine; In dichloromethane; for 2.0h;Cooling with ice;	A solution of cyclopropanecarbonyl chloride (0.54 g, 5.21 mmol) in DCM (10 mL) was added dropwise to an ice-cold solution of 5-bromo-lH-indol-7-amine (1.0 g, 4.74 mmol) and triethylamine (0.991 mL, 7.1 1 mmol) in DCM (20 mL), and the mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate and water. Separated organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography using 20% ethyl acetate in hexanes to afford the title compound (1.1 g, 76%) as a red solid. H NMR (300 MHz, DMSO- d6): δ 1 1.0 (s, 1H), 10.08 (s, 1H), 7.72 (s, 1H), 7.48 (s, 1H), 7.41 (t, J= 3.0 Hz, 1H), 6.43 (t, J= 2.4 Hz, 1H), 1.90 - 1.86 (m, 1H), 0.88 - 0.82 (m, 4H). ESI-MS m/z = 279 (M+H)+.

References: [1]Patent: US2014/148437,2014,A1 .Location in patent: Page/Page column 0258-0260.
[2]Patent: WO2014/81994,2014,A1 .Location in patent: Page/Page column 55.

2
[ 374537-99-2 ]
[ 1610801-26-7 ]