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

HRID 1914888Notes

Reaction equation

HRID 1914888 reaction equation
[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

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 2760919Cyclopropanesulfonyl chlorideHCID 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

Product 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-oneYield 42.1%

Procedure

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).

Sources & evidence

ORD record
ord-517f685e8ddc4d62bcc254d1f6a3fefe
Source dataset
uspto-grants-2013_12
Patent number
US08614239B2

Reaction notes

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