Cesium carbonate → HCID 67451383, compound
Reaction equation
[CH3:1][C:2]([C:6]1[NH:7][C:8](=[O:12])[CH:9]=[CH:10][CH:11]=1)([CH3:5])[C:3]#[N:4].Cl[C:14]([F:20])([F:19])C(OC)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[F:19][CH:14]([F:20])[O:12][C:8]1[N:7]=[C:6]([C:2]([CH3:1])([CH3:5])[C:3]#[N:4])[CH:11]=[CH:10][CH:9]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a 100 mL round bottom flask was added 2-methyl-2-(6-oxo-1,6-dihydropyridin-2-yl)propanenitrile (8.2 g, 51 mmol, 1.0 equiv), methyl chlorodifluoroacetate (14.9 g, 103 mmol, 2.0 equiv), cesium carbonate (23.3 g, 71 mmol, 1.4 equiv), and DMF (100 mL). The reaction was heated to 95° C. and stirred for 3 hours. The reaction was then quenched with water (100 mL) and diluted with EtOAc (500 mL). The organic layer was separated from the aqueous layer. The aqueous layer was extracted with EtOAc (100 mL), and the combined organic phases were washed with saturated brine solution (3×200 mL), dried over Na2SO4, concentrated, and chromatographed with silica gel (2-5% EtOAc/hex) to give 2-(6-(difluoromethoxy)pyridin-2-yl)-2-methylpropanenitrile (6.2 g, 57%) as a clear oil.
Workup
- customThe reaction was then quenched with water (100 mL)
- additiondiluted with EtOAc (500 mL)
- customThe organic layer was separated from the aqueous layer
- extractionThe aqueous layer was extracted with EtOAc (100 mL)
- washthe combined organic phases were washed with saturated brine solution (3×200 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customchromatographed with silica gel (2-5% EtOAc/hex)
Sources & evidence
- ORD record
- ord-07f8633119184a078cff493335b67e33
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018223B2
Reaction notes
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