Methyl iodide → tert-Butyl 4-(6-bromo-1-methyl-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate

Participants

Reaction Steps

Sodium hydride (60% in mineral oil, 7.1 mg, 0.178 mmol) was added to a solution of tert-butyl 4-(6-bromo-1H-pyrrolo[3,2-c]pyridin-2-yl)-1H-pyrazole-1-carboxylate (27) (43 mg, 0.118 mmol) in DMF (515 μL) at 0° C. The reaction mixture was then stirred for 30 min at 0° C. before the addition of iodomethane (18 μL, 0.237 mmol). After stirring for 30 min, it was diluted with water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated under reduced pressure. The crude was purified via Biotage (DCM/EtOAc 99/1 to 90/10; 12+M column) to afford the title compound as a white solid (35 mg, 78%). 1H NMR (500 MHz, CDCl3) 1.71 (s, 9H), 3.78 (s, 1H), 6.68 (d, J=0.6 Hz, 1H), 7.46 (m, 1H), 7.94 (d, J=0.6 Hz, 1H), 8.32 (d, J=0.6 Hz, 1H), 8.64 (s, 1H).

Provenance & Evidence