4-(3-Fluoro-phenyl)-1,3-dihydro-indol-2-one → HCID 25115602, compound

HRID 2191471Notes

Reaction equation

HRID 2191471 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:22]=[C:23]([C:27]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:28]=2[CH2:29][C:30](=[O:36])[NH:31]3)[CH:24]=[CH:25][CH:26]=1>>[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]=[C:29]3\[C:30](=[O:36])[NH:31][C:32]4[C:28]\3=[C:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[CH:22]=3)[CH:35]=[CH:34][CH:33]=4)=[C:14]([CH3:15])[C:7]=2[C:6]1=[O:18]

Participants

3

Reactant 2

HCID 225617564-(3-Fluoro-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 25115602HCID 25115602, compoundYield 38.9%

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-(3-fluoro-phenyl)-1,3-dihydro-indol-2-one as starting materials to obtain (Z)-5-(2-dimethylamino-ethyl)-2-[4-(3-fluoro-phenyl)-2-oxo-1,2-dihydro-indol-3-ylidenemethyl]-3-methyl-5,6,7,8-tetrahydro-1H-pyrrolo[3,2-c]azepin-4-one 41 (37 mg, yield 38.9%) as a yellow solid.

Workup

  1. customThe title compound was prepared under the same conditions

Sources & evidence

ORD record
ord-3577b21a57ab4b96b2fe6311b34aa898
Source dataset
uspto-grants-2012_12
Patent number
US08329682B2

Reaction notes

Loading…