Hydrochloric Acid → HCID 67251860, compound

Participants

Reaction Steps

To a solution of (1,6-dihydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)-acetic acid ethyl ester (2 g, 8 mmol) and methyl 2-chloro-5-pyrazinecarboxylate (1.95 g, 12 mmol) in DMF (40 mL) at 0° C. was added NaH (0.8 g, 20 mmol). The reaction mixture was allowed to warm up to room temperature slowly and heated at 50° C. for 1 h. The reaction mixture was cooled down and acidified to pH 3 with 6N HCl, extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=9:1) affording the title compound (1.9 g, 61%) as a light yellow solid. 1H NMR (CDCl3) δ 8.82 (s, 1H), 8.53 (s, 1H), 7.38 (d, 1H), 7.07 (d, 1H), 5.69 (dd, 1H), 4.10 (q, 2H), 4.02 (s, 3H), 3.06 (dd, 1H), 2.43 (m, 1H), 2.39 (s, 3H), 1.23 (t, 3H).

Provenance & Evidence