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

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. Bromomethylcyclopropane (78 uL, 108 mg, 0.8 mmole) was added and the reaction was stirred at room temperature for 6 hours. Ethyl acetate (25 mL) was added and the solution was washed with water (3×10 mL) and with brine (5 mL), dried and evaporated in vacuo. The crude product was purified using preparative TLC eluting with ethyl acetate to afford the title compound (98 mg, 82%). 1H-NMR (CDCl3, 500 MHz): δ 0.23 (m, 2H), 0.55 (m, 2H), 1.12 (m, 1H), 4.03 (s, 3H), 4.07 (d, J=6.31 Hz, 2H), 6.54 (d, J=0.95 Hz, 1H), 7.45 (t, J=0.95 Hz, 1H), 7.61 (s, 1H), 7.71 (d, J=0.95 Hz, 1H), 8.61 (d, J=0.95 Hz, 1H).

1. stirringthe reaction was stirred at room temperature for 6 hours
2. washthe solution was washed with water (3×10 mL) and with brine (5 mL)
3. customdried
4. customevaporated in vacuo
5. customThe crude product was purified
6. washeluting with ethyl acetate

ORD record

ord-8d3b6413f7c04148899e9fd828930265

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2