Boron tribromide → HCID 68840148, compound

HRID 230018Notes

Reaction equation

HRID 230018 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:31][CH2:30][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:28][CH2:27]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([O:24]C)=[CH:23][C:16]=2[N:15]=1)[C:5]([O:7][CH3:8])=[O:6].B(Br)(Br)Br>C(Cl)Cl.CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH2:12][N:13]([CH:26]1[CH2:27][CH2:28][CH:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:30][CH2:31]1)[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([OH:24])=[CH:23][C:16]=2[N:15]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 68837491Methyl 3-bromo-4-{[(4-tert-butylcyclohexyl)(5-methoxy-1-methyl-1H-benz-imidazol-2-yl)amino]methyl}benzoate

Product 1

HCID 68840148HCID 68840148, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring solution of the title compound of Example 224 Step D (0.1 mmol, 54 mg) in 1 mL of DCM cooled to −78° C. under N2 was added dropwise BBr3 (0.3 mmol, 0.3 mL of a 1M solution in DCM). The reaction was allowed to warm to ambient temperature. After 1 h the reaction was taken up in 10 mL of MeOH and then concentrated under reduced pressure. The residue was purified by flash chromatography on silica eluting with 50% EtOAc/hexanes, affording the product as a white solid. HPLC A: 2.54 min.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by flash chromatography on silica eluting with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-80b9fb64b6ee42f3af7c9aa3285e4bee
Source dataset
uspto-grants-2009_07
Patent number
US07563815B2

Reaction notes

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