Triphenylphosphine → 4-methoxy-2-oxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2-dihydropyridine-3-carbonitrile

HRID 1526380노트

반응식

HRID 1526380 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][NH:6][C:5](=[O:9])[C:4]=1[C:10]#[N:11].[S:12]1[CH2:17][CH2:16][CH:15](O)[CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(=O)([O-])O.[Na+].O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]([CH:15]2[CH2:16][CH2:17][S:12][CH2:13][CH2:14]2)[C:5](=[O:9])[C:4]=1[C:10]#[N:11]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 576296Tetrahydro-2H-thiopyran-4-olHCID 27867023-Pyridinecarbonitrile, 1,2-dihydro-4-methoxy-2-oxo-

생성물 1

HCID 1177702324-methoxy-2-oxo-1-(tetrahydro-2H-thiopyran-4-yl)-1,2-dihydropyridine-3-carbonitrile수율 19.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a mixture of 4-methoxy-2-oxo-1,2-dihydropyridine-3-carbonitrile (1.00 g), tetrahydro-2H-thiopyran-4-ol (1.18 g), triphenylphosphine (2.62 g) and tetrahydrofuran (30 mL) was added dropwise diisopropyl azodicarboxylate (2.02 g) at room temperature under nitrogen atmosphere, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted twice with ethyl acetate. The extracts were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (320 mg).

후처리

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-3ee9519ebdaa45ee82d64eab6a70de62
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085578B2

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