Diethyl Malonate → HCID 67113019, compound

Participants

Reaction Conditions

Reaction Steps

To a slurry of sodium hydride (0.206 g, 5.14 mmol) in 7 mL DMF was added diethyl malonate (0.690 mL, 4.57 mmol) dropwise via syringe (bubbling). After 3 min, the reaction mixture was clear, and solid 2-(4-(3-bromo-2-(bromomethyl)propyl)-2-fluorophenyl)-5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine (0.640 g, 1.14 mmol) was added, the reaction mixture was sealed, and heated to 100° C. After 1 h, the reaction mixture was partitioned between sat'd aq. NH4Cl and EtOAc. The org layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography, EA/hexanes gradient, to give diethyl 3-((3-fluoro-4-(5-(1-phenylcyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)cyclobutane-1,1-dicarboxylate as a white solid. MS (ESI) m/z: calculated: 558.2; Observed: 559.1 (M++1).

Provenance & Evidence