Sodium hydride → HCID 178419418, compound

Participants

Reaction Conditions

Reaction Steps

2-{2-[5-Bromo-4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-phenyl}-ethanol was dissolved in DMF (20 mL) and sodium hydride (100 mg) was added until the gas evolution stops. The mixture was stirred at 80° C. for 12 h. The reaction was quenched with saturated ammonium chloride solution (5 mL) and concentrated. The solid was suspended in water (20 mL) and was applied to a Varian chemelut cartridge and eluted with ethyl acetate. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes followed by mass triggered reverse phase HPLC to afford 5-Bromo-7,8-dihydro-2H-6-oxa-2,3-diaza-benzocycloocta[cd]indene (28.6 mg, 0.09 mmol, 23% yield). 1H NMR (500 MHz, MeCN-d3) δ 12.18 (s, 1H), 8.33 (s, 1H), 7.62 (d, J=2.5 Hz, 1H), 7.47 (m, 1H), 7.38 (m, 1H), 7.29 (m, 2H), 4.30 (t, J=6 Hz, 2H), 2.91 (t, J=6 Hz, 2H). MS: m/z 315.0/317.0 (M+H+) and 5-Bromo-2-(2-trimethylsilanyl-ethoxymethyl)-7,8-dihydro-2H-6-oxa-2,3-diaza-benzocycloocta[cd] indene (45 mg, 0.01 mmol, 26% yield).

Provenance & Evidence