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

HRID 474962Notes

Reaction equation

HRID 474962 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.[F:24][C:25]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:26]=1[CH2:27][O:28][C:29]1[CH:34]=[CH:33][NH:32][C:31](=[O:35])[CH:30]=1>>[F:24][C:25]1[CH:39]=[C:38]([F:40])[CH:37]=[CH:36][C:26]=1[CH2:27][O:28][C:29]1[CH:34]=[CH:33][N:32]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[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]=4[N:8]([CH3:11])[C:9]=3[CH:10]=2)[C:31](=[O:35])[CH:30]=1

Participants

3

Reactant 2

HCID 220503904-(2,4-difluorobenzyloxy)-1H-pyridin-2-oneHCID 66874851tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate

Product 1

HCID 70805146tert-Butyl 8-(4-(2,4-difluorobenzyloxy)-2-oxopyridin-1 (2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylateYield 59.2%

Procedure

tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (155 mg, 0.411 mmol) and 4-(2,4-difluorobenzyloxy)pyridin-2(1H)-one (97 mg, 0.41 mmol) was reacted following the procedure for Example 2 (step d) to provide the title compound (130 mg, 59%) as a green oil: ESI MS m/z 536 [M+H]+.

Sources & evidence

ORD record
ord-819f26dda125437d97a10b0af4ca3f6d
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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