Iodoethane → HCID 86683582, 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) in anhydrous N,N-dimethylformamide (1 mL) to give a yellow solution, then cooled to 0° C. under a nitrogen atmosphere. Sodium hydride, 60% in oil (10 mg, 0.254 mmol) was added and the mixture stirred at 0° C. for 15 minutes. Iodoethane (10 μl, 0.127 mmol) was added and the mixture stirred at 0° C. for 30 minutes, allowed to warm to room temperature then stirred for one hour. Further sodium hydride, 60% in oil (10.18 mg, 0.254 mmol) was added and the reaction mixture was heated to 40° C. under a nitrogen atmosphere for one hour. Further iodoethane (10 μl, 0.127 mmol) was added and the mixture stirred at room temperature for 30 minutes. The reaction mixture was quenched by the addition of saturated sodium bicarbonate solution (5 mL) and extracted into ethyl acetate (3×5 mL). The organic phase was washed with 50:50 water:brine (2×10 mL) then brine (10 mL), dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. The residue was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 88:12 to 0:100) to give the desired product as a pale yellow solid (7 mg, 13% yield). 1H-NMR (500 MHz, CDCl3) δ 7.10-7.28 (10H, m), 4.93 (1H, br s), 4.81 (2H, s), 3.94 (2H, q), 2.10-2.55 (4H, m), 1.90-2.08 (1H, m), 1.65-1.80 (1H, m), 1.00-1.40 (9H, br m), 1.14 (3H, t). LCMS (Method A) RT=7.29 min, M+H+=500.12.

Provenance & Evidence