Diethyl Malonate → HCID 67112866, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of NaH (0.55 g, 14 mmol) in 40 mL DME under nitrogen was added diethyl malonate (2.1 mL, 14 mmol) slowly dropwise. After addition of 1 mL, the reaction mixture was warm, so cooled to 0° C. and continued addition. To the resulting clear solution was added a slurry of 2-(4-(bromomethyl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)-thiazolo[5,4-b]pyridine (3.00 g, 6.8 mmol) as a solid. After 1 h, the reaction mixture was quenched with sat'd aq. Ammonium chloride and DCM, and the aq. Layer was extracted with DCM, and the combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography, 40 g, 0-30% EA/hexanes. Product containing fractions were combined and concentrated and triturated with hexanes to give diethyl 2-((3-fluoro-4-(5-(1-phenyl-cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)malonate as an off-white solid. MS (ESI) m/z: calculated: 518.2; Observed: 519.1 (M++1).

Provenance & Evidence