3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-{3-[Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

HRID 2242133노트

반응식

HRID 2242133 반응식
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13])=[O:2].[CH3:17][S:18][C:19]1[CH:24]=[CH:23][C:22]([Mg]Br)=[CH:21][CH:20]=1>C1COCC1>[OH:2][CH:1]([C:22]1[CH:23]=[CH:24][C:19]([S:18][CH3:17])=[CH:20][CH:21]=1)[C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:8]=1[C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[C:12]#[N:13]

참가 물질

4

반응물 2

HCID 592052083-(3-Formyl-pyridin-4-yl)-benzonitrileHCID 178503242HCID 178503242, 화합물

생성물 1

HCID 592051833-{3-[Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-(3-formyl-pyridin-4-yl)-benzonitrile (15 mg, 0.075 mmol) in THF (1 mL) at −78° C. was added 0.5 M 4-methylsulfanylphenylmagnesium bromide in THF (0.3 mL). The reaction mixture was quenched with ammonium chloride and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, concentrated, and the residue purified by flash chromatography eluted with 5% methanol in dichloromethane to yield 3-{3-[hydroxy-(4-methylsulfanyl-phenyl)-methyl]-pyridin-4-yl}-benzonitrile as white crystals.

후처리

  1. customThe reaction mixture was quenched with ammonium chloride
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customthe residue purified by flash chromatography
  6. washeluted with 5% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-1879bfb84fa04c2a91747d30f6b954de
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671065B2

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