Acetone → methyl 10-bromo-9-fluoro-3-(2-hydroxypropan-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

HRID 575328Notes

Reaction equation

HRID 575328 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.[CH3:22][C:23]([CH3:25])=[O:24]>>[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]([C:23]([OH:24])([CH3:25])[CH3:22])=[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 180AcetoneHCID 86693079Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 86693362methyl 10-bromo-9-fluoro-3-(2-hydroxypropan-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Procedure

Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate (0.3 g) was reacted with Acetone similar to as described in example 8 with non-critical modifications to produce methyl 10-bromo-9-fluoro-3-(2-hydroxypropan-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate. This crude intermediate was reacted via General Procedure L to provide 10-bromo-9-fluoro-3-(2-hydroxypropan-2-yl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide which was reacted as a crude with 2-Methyl-3-butyne-ol via General Procedure E to afford 23 mg (7%) of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-(1-hydroxy-1-methyl-ethyl)-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide. M+1=398.

Sources & evidence

ORD record
ord-8d26a7905b714d6dbd2e0dfbf4928535
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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