Triacetoxyperiodinane → 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-one

HRID 218180Notes

Reaction equation

HRID 218180 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:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:18]([CH3:23])([CH3:22])[CH:19]([OH:21])[CH3:20])=[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]([CH:17]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)[C:18]([CH3:23])([CH3:22])[C:19](=[O:21])[CH3:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 592510984-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-ol

Product 1

HCID 592511494-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-oneYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-ol (15 mg, 0.038 mmol) in DCM (1 ml) was treated with commercially available Dess-Martin periodinane (25 mg, 0.058 mmol). The reaction was complete in 45 minutes and was filtered through a plug of SiO2 using DCM/hexane (3:1) and concentrated to give the crude product. The crude material was purified via chromatography on silica gel eluting with 14% ethyl acetate in hexane to afford 4-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3,3-dimethyl-4-phenylbutan-2-one as a white foam (15 mg, quantitative yield). 1H NMR (400 MHz, MeOD) δ ppm 8.20 (1 H, s) 7.81 (1 H, s) 7.70 (2 H, dd, J=9.16, 4.58 Hz) 7.60 (1 H, d, J=8.65 Hz) 7.38 (1 H, dd, J=8.65, 1.53 Hz) 7.23-7.35 (6 H, m) 7.19 (1 H, t, J=7.12 Hz) 4.67 (1 H, s) 2.05 (3 H, s) 1.26 (6 H, d, J=5.09 Hz). LC/MS (m/z) 387.20 [(M+1)+]; HPLC Rt: 3.758 min.

Workup

  1. filtrationwas filtered through a plug of SiO2
  2. concentrationconcentrated
  3. customto give the crude product
  4. customThe crude material was purified via chromatography on silica gel eluting with 14% ethyl acetate in hexane

Sources & evidence

ORD record
ord-34005b21b3e9496aaa59c2f943af803c
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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