Water → 6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine

Participants

Reaction Conditions

Reaction Steps

Potassium t-butoxide (315 mg 2.81 mmole) was dissolved in NMP (3 mL) and 2-bromo-5-((1-methyl-1H-pyrazol-4-yl)ethynyl)pyridin-4-amine (24) (375 mg 1.35 mmole) was added to the stirred solution. The reaction was placed under nitrogen and warmed at 50° C. for 3 hours. The reaction was cooled and 10% ammonium chloride (3 mL) added. Water (21 mL) was heated to about 60° C. and the product solution in NMP/water was added to the water; a solid immediately crashes out. The suspension was allowed to cool to r.t., filtered and the solid washed with water. Drying in a vac desiccator over KOH for 3 days gave product (347 mg) which was azeotroped with ethanol (2×15 mL) and toluene (2×15 mL) to give the title compound (315 mg, 84%). 1H-NMR (d6-DMSO, 500 MHz): δ 3.90 (s, 3H), 6.69 (d, J=0.95 Hz, 1H), 7.47 (t, J=0.95 Hz, 1H), 7.94 (d, J=0.63 Hz, 1H), 8.18 (s, 1H), 8.50 (d, J=0.95 Hz, 1H), 11.92 (br s, 1H, NH).

Provenance & Evidence