2-Fluorophenylboronic acid → HCID 57537614, compound

Participants

Reaction Conditions

Reaction Steps

78 mg (0.14 mmol) of (5-[4-chloro-3-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide, 21 mg (0.15 mmol) of 2-fluoro-phenylboronic acid and 6 mg (7 μmol) of (1,1′-bis(diphenylphosphino)ferrocenepalladium(II)-dichloride dichloromethane adduct were dissolved in a mixture of 2.6 mL of acetonitrile, 2.6 mL of toluene and 1.5 mL of a saturated aqueous solution of sodium bicarbonate. The resulting mixture was heated to 110° C. in a closed vial for 22 h. The resulting mixture was diluted with ethyl acetate, dried over sodium sulfate and evaporated. The resulting crude was purified by flash chromatography on silica gel using a gradient of 10% v/v methanol in ethyl acetate and hexanes to afford 56.6 mg (0.10 mmol) of 5-[4-chloro-3-(2-fluoro-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-nicotinamide. 1H-NMR [500 MHz, d6-DMSO] δ: 8.73 (d, 1H), 8.67 (d, 1H), 8.41 (s, 1H), 7.99 (t, 1H), 7.97 (s, 1H), 7.49-7.41 (m, 2H), 7.30-7.25 (m, 2H), 5.74 (s, 2H), 3.62 (t, 2H), 3.01 (s, 3H), 2.97 (s, 3H), 0.86 (t, 2H), −0.06 (s, 9H); MS [MH+] m/z: 525.

Provenance & Evidence