Triacetoxyperiodinane → (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone
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]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[OH:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1Participants
4
Procedure
(1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (Example 1(f)) (2.4 g, 7.54 mmol) was dissolved in 50 mL of DCM and treated with Dess Martin periodinane (3.2 g, 7.54 mmol) and stirred overnight. The next day, the reaction was extracted from 2 M NaOH with DCM (vigorous shaking)×3, dried over MgSO4, filtered, and concentrated in vacuo. The crude material was filtered through a silica gel pad using EtOAc and concentrated to give (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone (2.4 g, 100%). MS found: (M+H)+=317.