4-(2,6-Difluoro-phenyl)-1,3-dihydro-indol-2-one → HCID 25115601, compound

HRID 2191470Notes

Reaction equation

HRID 2191470 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][N:5]1[CH2:11][CH2:10][CH2:9][C:8]2[NH:12][C:13]([CH:16]=O)=[C:14]([CH3:15])[C:7]=2[C:6]1=[O:18].[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1[CH2:30][C:31](=[O:37])[NH:32]2>>[F:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:22]=1[C:28]1[CH:36]=[CH:35][CH:34]=[C:33]2[C:29]=1/[C:30](=[CH:16]/[C:13]1[NH:12][C:8]3[CH2:9][CH2:10][CH2:11][N:5]([CH2:4][CH2:3][N:2]([CH3:19])[CH3:1])[C:6](=[O:18])[C:7]=3[C:14]=1[CH3:15])/[C:31](=[O:37])[NH:32]2

Participants

3

Reactant 2

HCID 225617464-(2,6-Difluoro-phenyl)-1,3-dihydro-indol-2-oneHCID 592500735-(2-Dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde

Product 1

HCID 25115601HCID 25115601, compoundYield 36.4%

Procedure

The title compound was prepared under the same conditions as described in step 4 of Example 23 with 5-(2-dimethylamino-ethyl)-3-methyl-4-oxo-1,4,5,6,7,8-hexahydro-pyrrolo[3,2-c]azepine-2-carbaldehyde 23c obtained from step 3 of Example 23 and 4-(2,6-difluoro-phenyl)-1,3-dihydro-indol-2-one as starting materials to obtain (Z)-2-[4-(2,6-difluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-5-(2-dimethylamino-ethyl)-3-methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 40 (36 mg, yield 36.4%) as an orange solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-67cf6ec03f0f4bcda11883476d5cd591
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

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