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Boron tribromide → n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-hydroxy-phenyl)-propionamide

HRID 413421
Notes
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Reaction equation

HRID 413421 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 18533208n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-methoxy-phenyl)-propionamide

Product 1

HCID 18533203n-[1-(4-Cyano-3-fluoro-phenyl)-1-(3-methyl-3h-imidazol-4-yl)-ethyl]-3-(3-hydroxy-phenyl)-propionamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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

  1. customAfter 10 min the ice bath was removed
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched with saturated NaHCO3 solution (25 mL)
  4. extractionextracted with EtOAc (3×50 mL)
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-55d1297a43a7485eb7d8aebccfdfda16
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06566385B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes