Sodium Hydroxide → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal

HRID 218156Notes

Reaction equation

HRID 218156 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:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]([CH3:22])([CH3:21])[CH2:19][OH: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.[OH-].[Na+]>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:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 687058683-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropan-1-ol

Product 1

HCID 592510413-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanalYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropan-1-ol (1.3 g, 3.5 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (2.12 g, 5.0 mmol) portionwise at RT under nitrogen. After stirring at RT for 24 hr, the mixture was poured into a 1N sodium hydroxide solution (100 mL), extracted with CH2Cl2 (100 mL), dried (Na2SO4) and concentrated. The crude residue was purified over silica gel eluting with EtOAc/hexanes (1:3) to give 1.03 g (79% yield) of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal, the NMR spectrum of which was consistent with the desired structure.

Workup

  1. extractionextracted with CH2Cl2 (100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified over silica gel eluting with EtOAc/hexanes (1:3)

Sources & evidence

ORD record
ord-b96b445d73664f88b8e60e33c732afba
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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