Ethyl bromoacetate → HCID 69789022, compound

Participants

Reaction Steps

3a-(4-Bromo-benzyl)-1-(3,5-dichlorophenyl)-1,3,3a,4,5,6-hexahydro-benzimidazol-2-one (190 mg) (0.42 mmol) in DMF (5 ml) was carefully dropped on a suspension of NaH 60% (20.2 mg) (1.2 eq) in DMF (5 ml) at RT. The reaction mixture was stirred 1 h at RT, then ethyl bromoacetate (0.094 ml) (2.0 eq) was added. After one night at RT, the mixture was heated to 100° C. for 8 h, then the reaction mixture was poured on water and extracted with tBuOMe. The organic layer was washed with water, dried over Na2SO4 and concentrated. The residue was purified on SiO2 chromatography (eluent EtOAc/cyclohexane—1/10) to give [7a-(4-Bromo-benzyl)-3-(3,5-dichlorophenyl)-2-oxo-2,3,5,6,7,7a-hexahydro-benzimidazol-3a-yl]-acetic acid ethyl ester (30.2 mg) as a yellow oil. 1H NMR (CDCl3): 7.35 (2H, d), 7.10 (1H, m), 6.95 (2H, d), 6.8 (2H, m), 4.95 (1H, m), 4.45 (1H, d), 4.2 (2H, q), 3.7 (1H, d), 2.9 (1H, d), 2.8 (1H, d), 2.45-2.1 (2H, m), 2.0-1.8 (4H, m), 1.25 (3H, t).

Provenance & Evidence