Boron tribromide → HCID 11639387, compound

HRID 1817502Notes

Reaction equation

HRID 1817502 reaction equation
[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[C:15]([F:18])([F:17])[F:16])[C:8]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27]C)[CH:22]=3)=[O:20])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][C:13]=3[C:15]([F:17])([F:18])[F:16])[C:8]([C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:27])[CH:22]=3)=[O:20])=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 69060133HCID 69060133, compound

Product 1

HCID 11639387HCID 11639387, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [1-cyclopentyl-7-(trifluoromethyl)-1H-indazol-3-yl](3-methoxyphenyl)methanone (0.19 g, 0.49 mmol) in 10 mL of CH2Cl2 containing 0.2 mL cyclohexene was cooled to −78° C. under an argon atmosphere. Boron tribromide (0.185 mL, 1.95 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 0.15 g of the title compound as a light yellow solid, (mp 152° C.).

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-59d8c3fb8ca04366af8f729c2226a67e
Source dataset
uspto-grants-2009_10
Patent number
US07598286B2

Reaction notes

Loading…