Methanol → 2-(3-(2-Fluoro-4-methylphenyl)-4-phenyl-1H-pyrazol-5-yl)ethanol
Reaction equation
[CH2:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:10]=2[F:16])[C:5]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:2]=C.ClCCl.[BH4-].[Na+].C[OH:29]>>[F:16][C:10]1[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=1[C:6]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:4]([CH2:1][CH2:2][OH:29])[NH:8][N:7]=1Participants
Procedure
5-Allyl-3-(2-fluoro-4-methylphenyl)-4-phenyl-1H-pyrazole (1.0 g, 3.42 mmol) was dissolved in methanol (40 mL) and dichloromethane (10 mL) and cooled to −78° C. on a dry-ice/acetone bath. Ozone was bubbled through the solution for 2 h, until the solution appeared light blue. To the reaction added sodium borohydride (0.129 g, 3.42 mmol) slowly. Upon complete addition, the reaction was removed from the dry-ice bath and stirred at room temperature for 1 h. Excess solvent was removed under reduced pressure and the reaction was extracted with EtOAc/H2O, dried over MgSO4, and purified by column chromatography to give the title compound as clear oil (0.70 g). LCMS m/z=297.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.30 (s, 3H), 2.79 (t, J=7.20 Hz, 2H), 3.62 (t, J=7.33 Hz, 2H), 6.93-7.00 (m, 1H), 7.09-7.14 (m, 2H), 7.15-7.23 (m, 3H), 7.25-7.31 (m, 2H), 12.86 (bs, 1H).
Workup
- customOzone was bubbled through the solution for 2 h, until the solution
- additionUpon complete addition
- customthe reaction was removed from the dry-ice bath
- customExcess solvent was removed under reduced pressure
- extractionthe reaction was extracted with EtOAc/H2O
- dry with materialdried over MgSO4
- custompurified by column chromatography
Sources & evidence
- ORD record
- ord-e5d5783cd9f44ddda6a88baf6e09a77b
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09012478B2
Reaction notes
Loading…