Sodium hydride → 6-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo [4',5':3,4]benzo[1,2-d]oxazol-7-one

반응식

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:22])=[C:14]([F:21])[C:15]4[N:16]=[C:17]([CH3:20])[O:18][C:19]=4[C:11]=3[NH:10][C:9]2=[O:23])=[C:4]([F:24])[CH:3]=1.[CH:25]1([S:28](Cl)(=[O:30])=[O:29])[CH2:27][CH2:26]1.[H-].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:22])=[C:14]([F:21])[C:15]4[N:16]=[C:17]([CH3:20])[O:18][C:19]=4[C:11]=3[N:10]([S:28]([CH:25]3[CH2:27][CH2:26]3)(=[O:30])=[O:29])[C:9]2=[O:23])=[C:4]([F:24])[CH:3]=1

참가 물질

반응물 3

HCID 24758Sodium hydride

HCID 2760919Cyclopropanesulfonyl chloride

HCID 672363876-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

생성물 1

HCID 672372936-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-2-methyl-6,8-dihydro-imidazo [4',5':3,4]benzo[1,2-d]oxazol-7-one수율 42.1%

실험 절차

Intermediate I-26a was prepared from 6-(4-bromo-2-fluoro-phenyl)-4,5-difluoro-2-methyl-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-17a: 200 mg, 0.52 mmol), cyclopropanesulfonyl chloride (111 mg, 0.781 mmol) and NaH (31.2 mg, 0.781 mmol) using procedures analogous to those described above for Intermediate I-19a to afford 110 mg of the product (42.1% yield). H1NMR (CDCl3, 300 MHz): δ 7.52-7.39 (m, 3H), 3.35-3.24 (m, 1H), 2.72 (s, 3H), 1.75-1.60 (m, 2H), 1.35-1.25 (m, 2H).