Boron tribromide → HCID 44480095, compound

HRID 2067973Notes

Reaction equation

HRID 2067973 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:20]=2[CH2:21][O:22]C)=[O:15])[CH2:10][CH2:11][CH3:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[F:31][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([C@@H:9]([NH:13][C:14]([C:16]2[CH:17]=[N:18][N:19]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:20]=2[CH2:21][OH:22])=[O:15])[CH2:10][CH2:11][CH3:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58443410HCID 58443410, compound

Product 1

HCID 44480095HCID 44480095, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-chloro-phenyl)-5-methoxymethyl-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-butyl]-amide (510 mg, 1.1 mmol) in CH2Cl2 (10 mL) is added BBr3 (1.0 M in CH2Cl2, 1.6 mL, 1.6 mmol) dropwise. After stiffing at room temperature for 1 hour, the reaction mixture is quenched with methanol (25 mL) and concentrated in vacuo. The crude material is purified by flash chromatography on silica gel (eluted with 20 to 60% EtOAc/hexanes) to afford 1-(4-chloro-phenyl)-5-hydroxymethyl-1H-pyrazole-4-carboxylic acid [(S)-1-(3-trifluoromethyl-phenyl)-butyl]-amide (510 mg, >99%).

Workup

  1. customthe reaction mixture is quenched with methanol (25 mL)
  2. concentrationconcentrated in vacuo
  3. customThe crude material is purified by flash chromatography on silica gel (eluted with 20 to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8b712f233d5d408590ae019dfaf57094
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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