3-(3-Formyl-pyridin-4-yl)-benzonitrile → 3-[3-[Hydroxy-(2,5-dimethoxy-phenyl)-methyl]-pyridin-4-yl)-benzonitrile

HRID 1712090노트

반응식

HRID 1712090 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].[O:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][C:20]=1[Mg]Br)[CH3:18]>C1COCC1>[OH:2][CH:1]([C:23]1[CH:24]=[C:19]([O:17][CH3:18])[CH:20]=[CH:21][C:22]=1[O:25][CH3:26])[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 178492591HCID 178492591, 화합물

생성물 1

HCID 684988763-[3-[Hydroxy-(2,5-dimethoxy-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 2,5-dimethoxylphenylmagnesium 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-(2,5-dimethoxy-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-96f9b496ff2143f1abdbf24d8a221b01
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07790895B2

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