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

Temperature

60 °C

6-bromo-2-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine (Preparation 22, 50 mg, 0.18 mmol) was dissolved in dry DMF (1 ml). The solution was degassed and a solution of sodium bis(trimethylsilyl)amide (0.27 ml of a 1M solution in THF, 0.27 mmol) was added. After 20 minutes reaction, 1-(bromomethyl)-4-fluorobenzene (51 mg, 0.27 mmol) was added and the reaction heated to 60° C. for 3 hours. The reaction was cooled to room temperature and diluted with ethyl acetate and water. The organic solution was washed with brine, dried over sodium sulphate and concentrated in vacuum. The crude product was purified on silica gel column chromatography eluting with 20% hexane in ethyl acetate to afford the title compound as white foam (50 mg, 71.9%). 1H-NMR (500 MHz, CDCl3) 3.92 (s, 3H), 5.31 (s, 2H), 6.62 (s, 1H), 6.93 (m, 2H), 7.02 (m, 2H), 7.27 (s, 1H), 7.39 (s, 1H), 7.51 (s, 1H), 8.63 (s, 1H).

1. customThe solution was degassed
2. additiona solution of sodium bis(trimethylsilyl)amide (0.27 ml of a 1M solution in THF, 0.27 mmol) was added
3. additionwas added
4. temperatureThe reaction was cooled to room temperature
5. washThe organic solution was washed with brine
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated in vacuum
8. customThe crude product was purified on silica gel column chromatography
9. washeluting with 20% hexane in ethyl acetate

ORD record

ord-d0dff2061bdd4a32bdaccaf4dbbb7f87

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09371319B2