Bromocyclopentane → HCID 86683589, 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 (50 mg, 0.106 mmol), potassium carbonate (44 mg, 0.318 mmol) and bromocyclopentane (0.034 mL, 0.318 mmol) in anhydrous N,N-dimethylformamide (1 mL) 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 (12 mg, 21% yield). 1H-NMR (500 MHz, CDCl3) δ 7.32 (1H, s), 7.17-7.28 (7H, m), 7.10-717 (2H, m), 4.94 (1H, br s), 4.83 (1H, quin), 4.72 (2H, s), 2.05-2.60 (6H, m), 1.83-2.03 (5H, m), 1.54-1.82 (3H, m), 1.00-1.45 (9H, br m). LCMS (Method A) RT=8.25 min, M+H+=540.19.

Provenance & Evidence