HCID 19862162, compound → HCID 66745521, compound

Participants

Reaction Conditions

Reaction Steps

N-(4-Chloro-3-formylpyridin-2-yl)pivalamide (678 mg, 2.82 mmol) and 3-oxo-N-(3-(trifluoromethyl)benzyl)butanamide (2.82 mmol) was dissolved in dry THF (25 ml) and cooled to 0° C. under an atmosphere of nitrogen. Potassium hexamethyldisilazane (14 ml, 7.0 mmol, 0.5 M in toluene) was added dropwise under 15 minutes and the reaction was stirred at 0° C. for 15 minutes followed by 18 hours at room temperature. Reaction was then diluted with NH4Cl (50 ml, sat aq) and extracted with CH2Cl2 (3*30 ml). Combined organics were dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2/CH3OH (20:1) as eluent to give 0.86 g (80%) of 5-chloro-2-methyl-N-(3-(trifluoromethyl)benzyl)-1,8-naphthyridine-3-carboxamide as a pale syrup.

Provenance & Evidence