3,4-Difluorobenzoyl chloride → 8-Dibenzylamino-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

HRID 37945Notes

Reaction equation

HRID 37945 reaction equation
[CH2:1]([N:8]([CH3:30])[C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:22]([CH3:24])([CH3:23])[CH2:21][NH:20][CH:19]=[C:18]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:14]=3[NH:15][C:16]=2[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=1[F:41])[C:35](Cl)=[O:36]>>[CH2:28]([O:27][C:25]([C:18]1[C:14]2[NH:15][C:16]3[CH:17]=[C:9]([N:8]([CH2:30][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[CH:10]=[CH:11][C:12]=3[C:13]=2[C:22]([CH3:24])([CH3:23])[CH2:21][N:20]([C:35](=[O:36])[C:34]2[CH:38]=[CH:39][C:40]([F:41])=[CH:32][CH:33]=2)[CH:19]=1)=[O:26])[CH3:29]

Participants

3

Reactant 2

HCID 27245193,4-Difluorobenzoyl chlorideHCID 11246670Azepino[4,5-b]indole-5-carboxylic acid, 1,2,3,6-tetrahydro-1,1-dimethyl-8-[methyl(phenylmethyl)amino]-, ethyl ester

Product 1

HCID 103938238-Dibenzylamino-3-(4-fluorobenzoyl)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylic acid ethyl ester

Procedure

In a manner similar to Example 2A, but using ethyl 8-(benzyl(methyl)amino)-1,1-dimethyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate and 3,4-difluorobenzoyl chloride, the following compound was prepared:

Workup

  1. customthe following compound was prepared

Sources & evidence

ORD record
ord-a23187c2687440c6bd0b1540d35269aa
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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