Boron tribromide → HCID 178519606, compound

HRID 1817498Notes

Reaction equation

HRID 1817498 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]([C:11]2[C:19]3[C:14](=[C:15]([C:20]([F:23])([F:22])[F:21])[CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178490436HCID 178490436, compound

Product 1

HCID 178519606HCID 178519606, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (3-methoxyphenyl)[7-(trifluoromethyl)-1H-indazol-3-yl]methanone (0.03 g, 0.094 mmol) in 2 mL of CH2Cl2 containing 0.2 mL cyclohexene was cooled to −78° C. under an argon atmosphere. Boron tribromide (0.035 mL, 0.375 mmol) was added in one portion and the reaction mixture was allowed to warm to ambient temperature. The reaction was quenched by the careful addition of methanol. The reaction mixture was partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). The solvents were removed in vacuo and the residue purified by flash chromatography to give 0.02 g of the title compound.

Workup

  1. customThe reaction was quenched by the careful addition of methanol
  2. customThe reaction mixture was partitioned with EtOAc and 1 N HCl
  3. washThe organic phase was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvents were removed in vacuo
  6. customthe residue purified by flash chromatography

Sources & evidence

ORD record
ord-94048bf3507f4ebd8dec63e16b1569da
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

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