4-Fluorobenzoyl chloride → n-Propyl 3(4-fluorobenzoyl)-2-methyl-8-fluoro-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

HRID 1723731Notes

Reaction equation

HRID 1723731 reaction equation
[CH2:1]([O:4][C:5]([C:7]1[C:13]2[NH:14][C:15]3[CH:16]=[C:17]([F:21])[CH:18]=[CH:19][C:20]=3[C:12]=2[CH2:11][CH:10]([CH3:22])[NH:9][CH:8]=1)=[O:6])[CH2:2][CH3:3].[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([N:9]2[CH:10]([CH3:22])[CH2:11][C:12]3[C:20]4[CH:19]=[CH:18][C:17]([F:21])=[CH:16][C:15]=4[NH:14][C:13]=3[C:7]([C:5]([O:4][CH2:1][CH2:2][CH3:3])=[O:6])=[CH:8]2)=[O:29])=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 666401122-Methyl-8-fluoro-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid n-propyl ester

Product 1

HCID 25121534n-Propyl 3(4-fluorobenzoyl)-2-methyl-8-fluoro-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

Procedure

The title compound was prepared in a manner similar to that described in Example 2A by using 2-methyl-8-fluoro-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylic acid n-propyl ester and 4-fluorobenzoyl chloride; 1H NMR (CDCl3) δ 10.47 (1H, s), 7.96 (1H, s), 7.61-7.65 (2H, m), 7.41 (1H, m), 7.17 (2H, t), 7.05 (1H, dd), 6.90 (1H, t), 5.63 (1H, m), 4.17 (2H, m), 4.05 (2H, m), 3.38 (1H, dd), 3.07 (1H, dd), 1.55 (2H, m), 1.07 (3H, d), 0.77 (3H, t); MS (ES): 425 (MH+).

Sources & evidence

ORD record
ord-ffea07bc72f144638d7cf2b9ce2e6a74
Source dataset
uspto-grants-2009_02
Patent number
US07485634B2

Reaction notes

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