Tetrabutylammonium Fluoride → HCID 72204422, compound

Participants

Reaction Steps

To a solution of 1-propan-2-yl-3-{4-[(trifluoromethyl)sulfonyl]phenyl}-1-[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]urea (167 mg, 0.29 mmol) in 1 mL THF was added 1 M tetrabutylammonium fluoride in THF (1.46 mL, 1.46 mmol). The reaction was heated to reflux for 1 h then treated with additional 1M tetrabutylammonium fluoride in THF (0.73 mL, 0.73 mmol). The solution was heated to reflux for 16 h, cooled to ambient temperature, and partitioned between saturated NaHCO3 and ethylacetate. The organics were washed with water and brine, then dried over Na2SO4, filtered and concentrated. The residue was purified on a Gilson reverse phase preparatory instrument, followed by purification by silica gel chromatography (CH2Cl2/MeOH followed by ethylacetate/hexanes) to give 1-(1-methylethyl)-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-3-{4-[(trifluoromethyl)sulfonyl]phenyl}urea. 1H NMR (400 MHz, CD3 OD): δ 8.19 (dd, J=4.8, 1.5 Hz, 1 H); 8.12 (dd, J=7.9, 1.5 Hz, 1 H); 7.90 (d, J=8.9 Hz, 2 H); 7.77 (d, J=9.0 Hz, 2 H); 7.33 (s, 1 H); 7.11 (dd, J=7.9, 4.8 Hz, 1 H); 4.79 (s, 2 H); 4.53-4.47 (m, 1 H); 1.25 (d, J=6.7 Hz, 6 H). LCMS [M+H]+=441.1.

Provenance & Evidence