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

HRID 563392노트

반응식

HRID 563392 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-162939de5250419d992c34007f545513
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067447B2

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