Hydrogen Bromide → HCID 123782459, compound

Participants

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 (35 mg, 0.07 mmol) in dry DMF (1 ml) was added sodium hydride (7 mg, 0.18 mmol) and 4-(bromomethyl)pyridine.HBr (23 mg, 0.09 mmol) under nitrogen. The resulting mixture was stirred for 1 hour at room temperature. A saturated solution of NaHCO3 was added and the mixture was extracted with dichloromethane (3×10 ml) using a phase separator (Isolute® SPE). The combined organic phases were concentrated to dryness under reduced pressure. The resulting residue was purified by Biotage silica gel chromatography (gradient 0 to 80% EtOAc in cyclohexane) to give the title compound (21 mg, 50%). 1H NMR (500 MHz, CDCl3): 8.54 (2H,s), 7.19-7.12 (9H,m), 6.97 (1H,S), 6.93-6.91 (2H,m), 5.11 (2H, s), 4.98 (1H, br s), 4.95 (2H, s), 2.52-2.20 (4H, m), 2.00-1.95 (1H, m), 1.75-1.70 (1H, m), 1.44-1.15 (9H, br).

Provenance & Evidence