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

HRID 1914887Notes

Reaction equation

HRID 1914887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:21])=[C:14]([F:20])[C:15]4[N:16]=[CH:17][O:18][C:19]=4[C:11]=3[NH:10][C:9]2=[O:22])=[C:4]([F:23])[CH:3]=1.[CH:24]1([S:27](Cl)(=[O:29])=[O:28])[CH2:26][CH2:25]1.[H-].[Na+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[C:13]([F:21])=[C:14]([F:20])[C:15]4[N:16]=[CH:17][O:18][C:19]=4[C:11]=3[N:10]([S:27]([CH:24]3[CH2:26][CH2:25]3)(=[O:29])=[O:28])[C:9]2=[O:22])=[C:4]([F:23])[CH:3]=1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2760919Cyclopropanesulfonyl chlorideHCID 672366336-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one

Product 1

HCID 672365846-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-oneYield 48.5%

Procedure

Intermediate I-25a was prepared from 6-(4-bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-16a: 220 mg, 0.57 mmol), cyclopropanesulfonyl chloride (120 mg, 0.86 mmol) and NaH (34 mg, 0.86 mmol) using procedures analogous to those described above for Intermediate I-19a to afford 135 mg of the product (48.5% yield). H1NMR (DMSO-d6, 300 MHz): δ 8.97 (s, 1H), 7.97 (dd, 1H), 7.80 (t, 1H), 7.70 (dd, 1H), 3.54-3.44 (m, 1H), 1.48-1.39 (m, 2H), 1.34-1.26 (m, 2H). HPLC: 94.1%

Sources & evidence

ORD record
ord-00ab844180ce4cf8befa997c2dd9915e
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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