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

HRID 474963Notes

Reaction equation

HRID 474963 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[C:26]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][NH:37][C:36](=[O:40])[CH:35]=2)=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1>>[Cl:24][C:25]1[C:26]([CH2:32][O:33][C:34]2[CH:39]=[CH:38][N:37]([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:36](=[O:40])[CH:35]=2)=[N:27][CH:28]=[C:29]([Cl:31])[CH:30]=1

Participants

3

Reactant 2

HCID 580933734-((3,5-dichloropyridin-2-yl)methoxy)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 123288157tert-Butyl 8-(4-((3,5-dichloropyridin-2-yl)methoxy)-2-oxopyridin-1(2H)-yl)-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H) carboxylateYield 66.5%

Procedure

tert-Butyl 8-bromo-6-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carboxylate (150 mg, 0.396 mmol) and 4-((3,5-dichloropyridin-2-yl)methoxy)pyridin-2(1H)-one (107 mg, 0.396 mmol) were reacted following the procedure for Example 2 (step d) to provide the title compound (150 mg, 66%) as a green oil: ESI MS m/z 569 [M+H]+.

Sources & evidence

ORD record
ord-34e65e4b34c8431dabffd055230112ff
Source dataset
uspto-grants-2014_01
Patent number
US08637501B2

Reaction notes

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