Lithium borohydride → (1-(4-fluorophenyl)-6-isopropyl-1H-indazol-5-yl)methanol
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:20](OC)=[O:21])=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Li+].[BH4-]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH2:20][OH:21])=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1Participants
4
Procedure
Methyl 1-(4-fluorophenyl)-6-isopropyl-1H-indazole-5-carboxylate (175 mg, 0.56 mmol) was dissolved in 5 mL THF and 1M LiBH4 in THF (3 mmol) was added. Heated at reflux. After 12 h, the reaction was quenched with MeOH, poured into brine and extracted with EtOAc×3. The organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified on SiO2 by MPLC using 1:3 EtOAc/hexane. Obtained 148 mg (93% yield) of (1-(4-fluorophenyl)-6-isopropyl-1H-indazol-5-yl)methanol. MS found: (M+H)+=285.