Water → 1,3-Benzenediol, 4-[1-(2-propenyl)-7-(trifluoromethyl)-1H-indazol-3-yl]-

HRID 1988496Notes

Reaction equation

HRID 1988496 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:13]([F:16])([F:15])[F:14])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][C:18]=2[O:25]C)=[N:5]1)[CH:2]=[CH2:3].C1CCCCC=1.B(Br)(Br)Br.O>C(Cl)Cl>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:13]([F:16])([F:15])[F:14])[C:6]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][C:18]=2[OH:25])=[N:5]1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8079CyclohexeneHCID 25134Boron tribromideHCID 116605201-allyl-3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole

Product 1

HCID 1354619821,3-Benzenediol, 4-[1-(2-propenyl)-7-(trifluoromethyl)-1H-indazol-3-yl]-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-allyl-3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole (0.065 g, 0.18 mmol) in CH2Cl2 containing 1.0 mL of cyclohexene at −78° C. was treated with boron tribromide (0.136 mL, 1.4 mmol) and slowly allowed to warm to ambient temperature. The reaction was quenched by dropwise edition of CH3OH to the cooled reaction. The solvent was removed in vacuo and the residue partitioned with EtOAc and 1 N HCl. The organic phase was washed with brine and dried (Na2SO4). Removal of the solvent in vacuo afforded the crude product. Pure product was obtained by crystallization or flash chromatography through water deactivated silica gel. A sample of 0.066 g was obtained as a white solid.

Workup

  1. customThe reaction was quenched by dropwise edition of CH3OH to the cooled reaction
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned with EtOAc and 1 N HCl
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customRemoval of the solvent in vacuo
  7. customafforded the crude product
  8. customA sample of 0.066 g was obtained as a white solid

Sources & evidence

ORD record
ord-f51e824775f74cff8a7509cfd836413f
Source dataset
uspto-grants-2009_06
Patent number
US07555415B2

Reaction notes

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