Boron tribromide → HCID 131732442, compound

HRID 1848742Notes

Reaction equation

HRID 1848742 reaction equation
B(Br)(Br)Br.[Br:5][C:6]1[CH:34]=[C:33]([F:35])[C:9]([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([O:20]C)[CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:8]([F:36])[CH:7]=1>C(Cl)Cl>[Br:5][C:6]1[CH:34]=[C:33]([F:35])[C:9]([CH2:10][N:11]2[C:15]3[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:14]=3[N:13]=[C:12]2[C@H:22]2[CH2:27][CH2:26][CH2:25][CH2:24][C@H:23]2[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:8]([F:36])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 131732443HCID 131732443, compound

Product 1

HCID 131732442HCID 131732442, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of BBr3 (5 mL, 1 M in DCM) was added to a mixture of racemic cis-ethyl 2-(1-(4-bromo-2,6-difluorobenzyl)-6-methoxy-1H-benzo[d]imidazol-2-yl)cyclohexanecarboxylate (1.5 g, 3.2 mmol) in CH2Cl2 (50 mL) at RT. The reaction mixture was stirred 1 h was and partitioned with H2O (50 mL). The organic layer was separated and concentrated to dryness. The resulting residue was purified by FCC to provide the title compound (110 mg, 87%). MS (ESI): mass calcd. for C23H23BrF2N2O3, 492.09; m/z found, 493.2 [M+H]+.

Workup

  1. custompartitioned with H2O (50 mL)
  2. customThe organic layer was separated
  3. concentrationconcentrated to dryness
  4. customThe resulting residue was purified by FCC

Sources & evidence

ORD record
ord-e7edd59d7dbf4efda6e371d49e3ae263
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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