Propargyl bromide → HCID 131734401, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl(1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (23 mg, 0.05 mmol) in dry DMF (1 mL) was added sodium hydride (3 mg, 0.05 mmol) at 0° C. under nitrogen. After 1 h at 0° C., propargyl bromide (16 μL, 0.15 mmol) was added and the resulting mixture was stirred for an additional 1 h at 0° C. A saturated solution of NH4Cl was added and the mixture was extracted with dichloromethane (3×) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by silica gel chromatography (gradient 0 to 30% EtOAc in cyclohexane) to give the title compound (17 mg, 68%). 1H NMR (500 MHz, CDCl3): 7.50 (1H, s), 7.31-7.24 (7H, m), 7.22-7.20 (2H,m), 5.01 (1H, br s), 4.92 (2H, s), 4.73 (2H, d), 2.55-2.25 (4H, m), 2.32 (1H, t), 2.09-2.01 (1H, m), 1.85-1.76 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence