Tetrahydrofuran → HCID 86706335, compound

Participants

Reaction Steps

6-Bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 100 mg, 0.36 mmole) was azeotroped with toluene (3 mL) and dissolved in DMF (1 mL). To the solution was added sodium hexamethyldisilazide, 1M in THF (0.4 mL, 0.4 mmole) and the reaction was stirred at room temperature for 20 minutes. Bromoethylmethyl ether (65 uL, 100 mg, 0.8 mmole) was added and the reaction was stirred at room temperature for 18 hours. The reaction was diluted with ethyl acetate (25 mL) and the solution washed with water (3×8 mL) and with brine, dried and evaporated to afford the title compound. 1H-NMR (CDCl3, 500 MHz): δ 3.31 (s, 3H), 3.72 (t, J=5.68 Hz, 2H), 4.01 (s, 3H), 4.28 (t, J=5.68 Hz, 2H), 6.54 (d, J=0.95 Hz, 1H), 7.48 (t, J=0.95 Hz, 1H), 7.71 (s, 1H), 7.74 (d, J=0.95 Hz, 1H), 8.60 (d, J=0.95 Hz, 1H).

Provenance & Evidence