Hydrogen Bromide → HCID 131732285, compound

HRID 1424825Notes

Reaction equation

HRID 1424825 reaction equation
N([O-])=O.[Na+].N[C:6]1[C:11]([F:12])=[CH:10][C:9]([N:13]([C:18]2[C:37]([CH:38]3[CH2:40][CH2:39]3)=[CH:36][C:21]3[C:22]([C:32]([NH:34][CH3:35])=[O:33])=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[O:24][C:20]=3[CH:19]=2)[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][C:7]=1[F:41].[BrH:42]>C(#N)C.CCOC(C)=O.O.[Cu]Br>[Br:42][C:6]1[C:11]([F:12])=[CH:10][C:9]([N:13]([C:18]2[C:37]([CH:38]3[CH2:40][CH2:39]3)=[CH:36][C:21]3[C:22]([C:32]([NH:34][CH3:35])=[O:33])=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)[O:24][C:20]=3[CH:19]=2)[S:14]([CH3:17])(=[O:16])=[O:15])=[CH:8][C:7]=1[F:41]

Participants

8

Reactant 3

HCID 260Hydrogen BromideHCID 23668193Sodium NitriteHCID 131732284HCID 131732284, compound

Product 1

HCID 131732285HCID 131732285, compoundYield 36%

Reagents, catalysts & solvents 4

HCID 24593copper(I) bromideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Sodium nitrite (0.034 g, 0.49 mmol) was added to a 0° C. solution of 6-(N-(4-amino-3,5-difluorophenyl)methylsulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methylbenzofuran-3-carboxamide (0.235 g, 0.444 mmol) in Acetonitrile (3 ml) and aq HBr (48%) (3 mL). The reaction mixture was stirred for 30 min at 0° C. and copper (I) bromide (0.076 g, 0.53 mmol) was added. The reaction mixture was stirred at 90° C. for 2 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 (0.094 g, 36%) as a white foam. LCMS (m/z, ES+)=593.2, 595.2 (M+H+).

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 2 h
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. custompurified by silica gel chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-355ac1cc451b4196b4faf9ea6bd372f2
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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