Cyclohexene → 1,3-Benzenediol, 4-[1-(2-propenyl)-7-(trifluoromethyl)-1H-indazol-3-yl]-
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].B(Br)(Br)Br.C1CCCCC=1>>[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
4
Procedure
1-Allyl-3-(2,4-dimethoxyphenyl)-7-(trifluoromethyl)-1H-indazole (0.065 g, 0.18 mmol) was treated with boron tribromide (0.136 mL, 1.4 mmol) and 1.0 mL of cyclohexene at −78° C. and then slowly allowed to warm to ambient temperature. The reaction was quenched by dropwise addition of methanol to the cooled reaction. The solvent was removed and the residue portioned with EtOAc and 1N HCl. The organic phase was washed with brine and dried with Na2SO4). Removal of the solvent in vacuo afforded the crude product. Pure product was obtained by crystallization to give the product (0.066 g) as a white solid, mp 114-115° C.;
Workup
- customThe reaction was quenched by dropwise addition of methanol to the cooled reaction
- customThe solvent was removed
- washThe organic phase was washed with brine
- dry with materialdried with Na2SO4)
- customRemoval of the solvent in vacuo
- customafforded the crude product
- customPure product was obtained by crystallization
Sources & evidence
- ORD record
- ord-9ce6bb18007140f8accf02a4cab29b04
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601847B2
Reaction notes
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