Sodium hydride → HCID 67253812, 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 (3.68 g, 20.0 mmol) in THF (60 mL) was treated with NaH (1.20 g, 30.0 mmol) at 0° C. The resulting suspension was stirred at room temperature 15 min and 5-bromo-pyrazine-2-carbonitrile was added. The reaction was stirred at room temperature for 3 h. The suspension was quenched with 1N HCl and extracted with ethyl acetate. The organic phase was separated, dried (Na2SO4), and concentrated. The residue was purified by the flash column chromatography (silica, hexanes/ethyl acetate=1:1) to afford the title compound (1.63 g). 1H NMR (300 MHz, CD3OD) δ 8.58 (s, 1H), 8.55 (s, 1H), 7.29 (s, 1H), 7.16 (s, 1H), 5.73-5.69 (m, 1H), 4.16 (q, 2H), 3.27-3.18 (m, 1H), 2.56-2.48 (m, 1H), 2.41 (s, 3H), 1.23 (t, 3H). MS found: (M+H)+=354.1.

Provenance & Evidence