Benzaldehyde → phenyl(3-phenyl-1H-indazol-6-yl)methanol

HRID 563392Notes

Reaction equation

HRID 563392 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([CH:22]([C:2]2[CH:10]=[C:9]3[C:5]([C:6]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[N:7][NH:8]3)=[CH:4][CH:3]=2)[OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 573551936-Bromo-3-phenyl-1H-indazoleHCID 178418339Butyllithium

Product 1

HCID 59252831phenyl(3-phenyl-1H-indazol-6-yl)methanolYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 6-bromo-3-phenyl-1H-indazole (109 mg, 0.40 mmol) in anhydrous THF (3 mL) was added n-butyl lithium solution (2M in hexanes, 0.47 mL, 0.94 mmol) dropwise at −78° C. under argon. The reaction mixture was stirred at −78° C. for 30 min and at −40° C. for 6 min before benzaldehyde (0.1 mL, 1 mmol) was added at −40° C. The reaction mixture was then stirred at rt for 1 hr. quenched with saturated aqueous ammonium chloride solution (5 mL) and extracted with ethyl acetate (10 mL). The ethyl acetate extract was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave phenyl(3-phenyl-1H-indazol-6-yl)methanol (71 mg, 0.24 mmol, 59% yield) as a solid.

Workup

  1. additionwas added at −40° C
  2. customquenched with saturated aqueous ammonium chloride solution (5 mL)
  3. extractionextracted with ethyl acetate (10 mL)
  4. extractionThe ethyl acetate extract
  5. dry with materialwas dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-162939de5250419d992c34007f545513
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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