5-Fluoro-2-methoxynicotinaldehyde → Methyl 10-bromo-9-fluoro-3-((5-fluoro-2-methoxypyridin-3-yl)(hydroxy)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

HRID 575419Notes

Reaction equation

HRID 575419 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:20]=1.[F:22][C:23]1[CH:24]=[C:25]([CH:31]=[O:32])[C:26]([O:29][CH3:30])=[N:27][CH:28]=1>>[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([CH:31]([C:25]4[C:26]([O:29][CH3:30])=[N:27][CH:28]=[C:23]([F:22])[CH:24]=4)[OH:32])=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:20]=1

Participants

3

Reactant 2

HCID 226783235-Fluoro-2-methoxynicotinaldehydeHCID 86693079Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 86693473Methyl 10-bromo-9-fluoro-3-((5-fluoro-2-methoxypyridin-3-yl)(hydroxy)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylateYield 68%

Procedure

Methyl 10-bromo-9-fluoro-3-((5-fluoro-2-methoxypyridin-3-yl)(hydroxy)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was prepared similarly according to the procedure in Example 9. Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was reacted with 5-fluoro-2-methoxy-pyridine-3-carbaldehyde to afford 196 mg (68% yield) of the title compound.

Workup

  1. customMethyl 10-bromo-9-fluoro-3-((5-fluoro-2-methoxypyridin-3-yl)(hydroxy)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was prepared similarly

Sources & evidence

ORD record
ord-6e7ee3a3cc834dc99e8dfcbb730cdd9c
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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