Potassium tert-butoxide → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][CH3:11])[C:5]([NH2:8])=[N:6][CH:7]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:9]=[C:10]([CH3:11])[NH:8][C:5]2=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
5-Bromo-3-prop-1-ynyl-pyridin-2-ylamine (91 g, 431 mmol) was treated with a 1M solution of potassium tert-butoxide in tert-butanol (700 mL) and the reaction mixture was heated at 85 OC 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) and evaporated then triturated with diethyl ether to afford the title compound as a brown solid (88.7 g, 97%). 1H NMR (400 MHz, CDCl3): 10.21 (s, 1H), 8.22 (d, J=2.1 Hz, 1H), 7.91 (d, J=2.1 Hz, 1H), 6.13 (s, 1H), 2.52 (s, 3H).