Isopropyl iodide → HCID 86683588, compound

Participants

Reaction Conditions

Reaction Steps

In a 15 mL reaction tube was added tert-butyl 1-(4-(2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutylcarbamate (25 mg, 0.053 mmol), potassium carbonate (22 mg, 0.159 mmol) and 2-iodopropane (16 μl, 0.159 mmol) in anhydrous N,N-dimethylformamide (500 μl) to give an orange suspension. The reaction mixture was stirred at 80° C. for one hour. The reaction mixture was allowed to cool to room temperature, diluted with saturated sodium bicarbonate solution (5 ml) and extracted into dichloromethane (3×3 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a yellow oil. This was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80) to give the desired product as an off-white solid (13 mg, 48% yield). 1H-NMR (500 MHz, CDCl3) δ 7.37 (1H, s), 7.10-7.28 (9H, m), 4.95 (1H, br s), 4.65-4.77 (3H, m), 2.05-2.60 (4H, m), 1.92-2.06 (1H, m), 1.65-1.80 (1H, m), 1.50 (6H, d), 1.00-1.45 (9H, br m). LCMS (Method A) RT=7.73 min, M+H+=514.15.

Provenance & Evidence