4-Fluorobenzoyl chloride → Ethyl 3-(4-fluorobenzoyl)-1-methyl-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylate

HRID 1258051Notes

Reaction equation

HRID 1258051 reaction equation
[CH3:1][CH:2]1[C:15]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7]=2[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5][NH:4][CH2:3]1.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([N:4]2[CH2:3][CH:2]([CH3:1])[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]2)=[O:27])=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 25223262Ethyl 1-methyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

Product 1

HCID 10000577Ethyl 3-(4-fluorobenzoyl)-1-methyl-1,2,3,6-tetrahydro-azepino[4,5-b]indole-5-carboxylate

Procedure

In a manner similar to Example 2, the title compound was prepared from ethyl 1-methyl-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate and 4-fluorobenzoyl chloride. 1H-NMR (CDCl3): δ 10.54 (1H, br s), 7.97 (1H, s), 7.63-7.68 (2H, m), 7.58 (1H, d), 7.39 (1H, d), 7.09-7.23 (4H, m), 5.28 (1H, dd), 4.25 (2H, m), 3.85 (1H, m), 3.18 (1H, d), 1.34 (3H, d), 1.22 (3H, t); MS(ESI): 393 (MH+).

Sources & evidence

ORD record
ord-3a361059a06946fa81f61595ea436c95
Source dataset
uspto-grants-2013_06
Patent number
US08466143B2

Reaction notes

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