Methyl bromoacetate → HCID 68182935, compound

Participants

Reaction Steps

To a mixture of 4-(4-chlorophenyl)-2-morpholino-5,6-dihydrothieno[2,3-c]pyridin-7(4H)-one (451 mg, 1.29 mmol) in THF (7.0 mL) in an ice bath was added 1.00 M potassium t-butoxide in THF (1.42 mL, 1.42 mmol) and the resulting solution was stirred in the ice bath for 30 minutes. Methyl bromoacetate (184 uL, 1.94 mmol) was added and the solution was stirred for 1 hour in the ice bath. The reaction was quenched with saturated NH4Cl (10 mL) and diluted with ethyl acetate (20 mL). The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→40/60) to give 455 mg (84% yield) of the title compound as a light yellow oil. LC/MS (FA) ES+ 421. 1H NMR (400 MHz, CDCl3) δ: 7.15-7.12 (m, 2H), 7.03-7.00 (m, 2H), 5.38 (s, 1H), 4.09 (d, 1H, J=17.2 Hz), 4.06-4.01 (m, 1H), 3.99 (d, 1H, J=17.2 Hz), 3.63-3.61 (m, 4H), 3.57-3.53 (m, 2H), 3.52 (s, 3H), 2.99-2.97 (m, 4H).

Provenance & Evidence