Hydrogen Bromide → HCID 131732282, compound
Reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:17]2[C:36]([CH:37]3[CH2:39][CH2:38]3)=[CH:35][C:20]3[C:21]([C:31]([NH:33][CH3:34])=[O:32])=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[O:23][C:19]=3[CH:18]=2)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:7]=1[C:40]([F:43])([F:42])[F:41].[BrH:44]>C(#N)C.CCOC(C)=O.O.[Cu]Br>[Br:44][C:6]1[CH:11]=[CH:10][C:9]([N:12]([C:17]2[C:36]([CH:37]3[CH2:39][CH2:38]3)=[CH:35][C:20]3[C:21]([C:31]([NH:33][CH3:34])=[O:32])=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[O:23][C:19]=3[CH:18]=2)[S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:7]=1[C:40]([F:43])([F:42])[F:41]Participants
8
Conditions
- Temperature
- 0 °C
Procedure
Sodium nitrite (0.18 g, 2.55 mmol) was added to a 0° C. solution of 6-(N-(4-amino-3-(trifluoromethyl)phenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (1.3 g, 2.32 mmol) in acetonitrile (14 ml) and aq HBr (48%) (14 mL). The reaction mixture was stirred for 30 min at 0° C. and copper (I) bromide (0.40 g, 2.78 mmol) was added. The reaction mixture was stirred at 60° C. for 1 h and diluted with EtOAc and water. The organic layer was washed with brine, dried (Na2SO4), filtered, evaporated and purified by silica gel chromatography (0-50% EtOAc/hexanes) to afford the title compound (1.06 g, 73%) as a white foam. LCMS (m/z, ES+)=625.2, 627.2 (M+H+).
Workup
- stirringThe reaction mixture was stirred at 60° C. for 1 h
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- customevaporated
- custompurified by silica gel chromatography (0-50% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-4d7377a8573843b09e1095c81d10467f
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927593B2
Reaction notes
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