Sodium hydride → HCID 118877923, compound

HRID 56885Notes

Reaction equation

HRID 56885 reaction equation
[H-].[Na+].[CH3:3][C:4]1([CH:8]=O)[CH2:7][O:6][CH2:5]1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:34]#[N:35])=[C:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]([CH2:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:19](=[O:33])[CH:18]=2)[CH:16]=1>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([C:34]#[N:35])=[C:15]([C:17]2[C:22]([O:23][CH3:24])=[CH:21][N:20]([C:25](=[CH:8][C:4]3([CH3:3])[CH2:5][O:6][CH2:7]3)[C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[C:19](=[O:33])[CH:18]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 189624683-Methyloxetane-3-carbaldehydeHCID 117622654tert-Butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate

Product 1

HCID 118877923HCID 118877923, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

64.0 mg (1.60 mmol, 60% in mineral oil) of sodium hydride and 200 mg (2.00 mmol) of 3-methyloxetane-3-carbaldehyde in 1 ml of dimethylformamide were added in succession to a solution of 300 mg (800 μmol) of tert-butyl [4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]acetate in 9 ml of dimethylformamide. After 15 min at room temperature, the reaction was terminated by addition of saturated aqueous ammonium chloride solution and the reaction mixture was then extracted three times with 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (24 g silica cartridge, flow rate 35 ml/min, cyclohexane/ethyl acetate gradient). Yield: 356 mg (96% of theory)

Workup

  1. customthe reaction was terminated by addition of saturated aqueous ammonium chloride solution
  2. extractionthe reaction mixture was then extracted three times with 20 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by flash chromatography (24 g silica cartridge, flow rate 35 ml/min, cyclohexane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-b2367fc66d0b4b04bc4685dbc6678ba4
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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