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

HRID 1526380Notes

Reaction equation

HRID 1526380 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-3ee9519ebdaa45ee82d64eab6a70de62
Source dataset
uspto-grants-2015_07
Patent number
US09085578B2

Reaction notes

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