Ethyl bromoacetate → HCID 86683580, 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 red solution, then cooled to 0° C. under a nitrogen atmosphere. Sodium hydride, 60% in oil (6.4 mg, 0.159 mmol) was added and the mixture stirred at 0° C. for 15 minutes. Ethyl 2-bromoacetate (0.035 mL, 0.318 mmol) was added and the mixture stirred at 0° C. for 30 minutes, allowed to warm to room temperature then stirred for one hour. The reaction mixture was quenched by the addition of saturated ammonium chloride solution (5 mL) and extracted into ethyl acetate (3×3 mL). The organic phase was washed with 50:50 water:brine (2×5 mL) then brine (5 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 an off-white solid (22 mg, 39% yield). 1H-NMR (500 MHz, CDCl3) δ 7.13-7.28 (8H, m), 7.37-7.43 (2H, m), 5.24 (1H, br s), 5.18 (2H, s), 4.89 (2H, s), 4.49 (2H, q), 2.40-2.90 (4H, m), 2.21-2.35 (1H, m), 1.90-2.10 (1H, m), 1.20-1.75 (9H, br m), 1.53 (3H, t). LCMS (Method A) RT=7.20 min, M+H+=558.13.

Provenance & Evidence