Diethyl Ether → 4-bromo-5H,6H,7H-cyclopenta[c]pyridin-7-one

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Reaction Steps

The crude sodium 4-bromo-6-(methoxycarbonyl)-5H-cyclopenta[c]pyridin-7-olate (20.0 mmol) was dissolved in aq. 6 M HCl, (54 mL) and heated at reflux for 1.5 h. The acidic solution was cooled in ice, poured into Et2O, basified with aq. 6 M KOH (to give a pH of −9) and extracted with Et2O (2×). The Et2O phases were collected, dried over Na2SO4, concentrated and purified by flash chromatography (20 g SiO2, i-PrOH (1%)/CH2Cl2) to afford after trituration with a small amount of Et2O the title compound (0.69 g, 16% over 2 steps) as pink solid. MS: 212.0 (M+H−, 1 Br).

Provenance & Evidence