Boron tribromide → n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-hydroxy-phenyl)-propionamide
Reaction equation
B(Br)(Br)Br.[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31]C)[CH:26]=2)([C:15]2[N:16]([CH3:20])[CH:17]=[N:18][CH:19]=2)[CH3:14])=[CH:9][C:8]=1[F:34])#[N:6]>C(Cl)(Cl)Cl>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([NH:21][C:22](=[O:33])[CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)([C:15]2[N:16]([CH3:20])[CH:17]=[N:18][CH:19]=2)[CH3:14])=[CH:9][C:8]=1[F:34])#[N:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
BBr3 (1M in CH2Cl2 ) (4 mL) was added slowly to a solution of N-[1-(4-cyano-3-fluoro-phenyl)-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-3-(3-methoxy-phenyl)-propionamide (0.123 g, 0.25 mmol) in CHCl3 (2 mL) at 0° C. After 10 min the ice bath was removed and the mixture stirred at 20° C. for 20 min. The mixture was cooled to 0° C., quenched with saturated NaHCO3 solution (25 mL), then extracted with EtOAc (3×50 mL). The organic layers were combined, washed with water, brine, dried (Na2SO4), filtered, and concentrated to give the title compound.
Workup
- customAfter 10 min the ice bath was removed
- temperatureThe mixture was cooled to 0° C.
- customquenched with saturated NaHCO3 solution (25 mL)
- extractionextracted with EtOAc (3×50 mL)
- washwashed with water, brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-55d1297a43a7485eb7d8aebccfdfda16
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06566385B2
Reaction notes
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