Potassium tert-butoxide → 5-Chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

5-Chloro-3-prop-1-ynyl-pyridin-2-ylamine (53.7 g, 0.32 mol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (515 mL) and the reaction mixture was heated at 85° C. for 1 hour. The mixture was then allowed to cool to ambient temperature and poured onto a 1:1 mixture of water/ice (ca. 1 L). The resultant precipitate was collected by filtration, washed with water and left to air dry. The resultant solid was dissolved in dichloromethane, dried (Na2SO4), filtered and evaporated then triturated with diethyl ether to afford the title compound as a grey solid (44.8 g, 83%). LCMS (Method B): RT=3.64 min, M+H+=167/169. 1H NMR (400 MHz, DMSO-d6): 8.02 (d, J=2.4 Hz, 1H), 7.83 (d, J=2.4 Hz, 1H), 6.11 (d, J=1.1 Hz, 1H), 2.40 (d, J=1.0 Hz, 3H).

Provenance & Evidence