Allyl bromide → HCID 68294911, compound

Participants

Reaction Steps

A solution of methyl 2-(4-(2,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)acetate (60 mg, 0.179 mmol) in tetrahydrofuran (THF) (2 mL) was treated with LiHMDS (0.358 mL, 0.358 mmol) and allyl bromide (0.232 mL, 2.68 mmol) at 0° C. The mixture was warmed to room temperature and stirred for 1 hour. The mixture was quenched with saturated NH4Cl solution and extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered and concentrated. The material was used crude in the next step (64 mg, 95%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.44-8.54 (m, 1 H) 7.41-7.56 (m, 2 H) 7.06-7.19 (m, 2 H) 6.97-7.05 (m, 1 H) 6.80-6.91 (m, 1 H) 5.40-5.70 (m, 1 H) 4.85-5.06 (m, 2 H) 3.89-4.05 (m, 1 H) 3.68 (s, 3 H) 3.53 (s, 3 H) 2.91-3.06 (m, 1 H) 2.43-2.55 (m, 1 H) 2.41 (s, 3 H) 2.03 (s, 3 H). LC/MS (m/z) ES+=376 (M+1).

Provenance & Evidence