4-(2,3-Difluoro-phenyl)-1,3-dihydro-indol-2-one → HCID 25114045, compound

HRID 2191412Notes

Reaction equation

HRID 2191412 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:13][C:14]([CH:17]=O)=[C:15]([CH3:16])[C:8]=2[C:7]1=[O:19])[CH3:2].[F:22][C:23]1[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=1[C:30]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:31]=1[CH2:32][C:33](=[O:39])[NH:34]2>>[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][CH2:5][N:6]1[CH2:12][CH2:11][CH2:10][C:9]2[NH:13][C:14](/[CH:17]=[C:32]3\[C:33](=[O:39])[NH:34][C:35]4[C:31]\3=[C:30]([C:24]3[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=3[F:22])[CH:38]=[CH:37][CH:36]=4)=[C:15]([CH3:16])[C:8]=2[C:7]1=[O:19])[CH3:2]

Participants

3

Reactant 2

HCID 225619714-(2,3-Difluoro-phenyl)-1,3-dihydro-indol-2-oneHCID 592500815-(2-Diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 25114045HCID 25114045, compoundYield 61.4%

Procedure

The title compound was prepared under the same conditions as described in step 10 of Example 1 with 5-(2-diethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 1j obtained from step 9 of Example 1 and 4-(2,3-difluoro-phenyl)-1,3-dihydro-indol-2-one 6d as starting materials to obtain (Z)-5-(2-diethylamino-ethyl)-2-[4-(2,3-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 6 (43 mg, yield 61.4%) as a yellow solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-c999e221f7a84a29a74752ae866222fc
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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