4-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-one → tert-Butyl 8-(4-(4-chloro-2-fluorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H) carboxylate

HRID 474964Notes

Reaction equation

HRID 474964 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][C:7]=3[N:8]([CH3:11])[C:9]=2[CH:10]=1.[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][O:30][C:31]2[CH:36]=[CH:35][NH:34][C:33](=[O:37])[CH:32]=2)=[C:27]([F:40])[CH:26]=1>>[Cl:24][C:25]1[CH:39]=[CH:38][C:28]([CH2:29][O:30][C:31]2[CH:36]=[CH:35][N:34]([C:2]3[CH:3]=[CH:4][C:5]4[C:6]5[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][C:7]=5[N:8]([CH3:11])[C:9]=4[CH:10]=3)[C:33](=[O:37])[CH:32]=2)=[C:27]([F:40])[CH:26]=1

Participants

3

Reactant 2

HCID 580922574-(4-Chloro-2-fluorobenzyloxy)pyridin-2(1H)-oneHCID 66874851tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 123529250tert-Butyl 8-(4-(4-chloro-2-fluorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H) carboxylateYield 48.5%

Procedure

tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (150 mg, 0.400 mmol) and 4-(4-chloro-2-fluorobenzyloxy)pyridin-2(1H)-one (101 mg, 0.400 mmol) were reacted following the procedure for Example 2 (step d) to provide the title compound (107 mg, 48%) as a yellow oil: ESI MS m/z 552 [M+H]+.

Sources & evidence

ORD record
ord-7a3ef55798184ed4994f5a35fc1b68ed
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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