7-Bromo-5-fluoroindolin-2-one → HCID 25116293, compound

HRID 2191492Notes

Reaction equation

HRID 2191492 reaction equation
[CH3:1][C:2]1[C:6]2[C:7](=[O:20])[N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:9][CH2:10][CH2:11][C:5]=2[NH:4][C:3]=1[CH:21]=O.[Br:23][C:24]1[CH:25]=[C:26]([F:34])[CH:27]=[C:28]2[C:32]=1[NH:31][C:30](=[O:33])[CH2:29]2>>[Br:23][C:24]1[CH:25]=[C:26]([F:34])[CH:27]=[C:28]2[C:32]=1[NH:31][C:30](=[O:33])/[C:29]/2=[CH:21]\[C:3]1[NH:4][C:5]2[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][N:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[C:7](=[O:20])[C:6]=2[C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 534188887-Bromo-5-fluoroindolin-2-oneHCID 592500973-Methyl-4-oxo-5-(2-piperidin-1-yl-ethyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 25116293HCID 25116293, compoundYield 76.44%

Procedure

The title compound was prepared under the same conditions as described in step 5 of Example 32 with 3-methyl-4-oxo-5-(2-piperidin-1-yl-ethyl)-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 32d obtained from step 4 of Example 32 and 7-bromo-5-fluoro-1,3-dihydro-indol-2-one 4b obtained from step 1 of Example 4 as starting materials to obtain (Z)-2-(7-bromo-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-3-methyl-5-(2-piperidin-1-yl-ethyl)-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 56 (63 mg, yield 76.44%) as a yellow solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-10759c93f5f84853a3c20a779f2424d9
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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