Sodium Carbonate → 2-(1-(3-fluoro-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Steps

A suspension of toluene-4-sulfonic acid-1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-3-methyl-but-1-enyl ester (prepared as in Example 130, 3.0 g, 6.05 mmol), 3-fluoro-phenylboronic acid (2.1 g, 15 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.42 g, 0.6 mmol) in dioxane (30 mL) and an aqueous sodium carbonate solution (2N, 15 mL) was heated at 90° C. in a microwave for 2 h. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with a saturated aqueous sodium bicarbonate solution (2×50 mL). The organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (40 g, 17% ethyl acetate/petroleum ether) afforded 2-(1-(3-fluoro-phenyl)-3-methyl-but-1-enyl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (2.6 g, 88%) as an off-white solid: 1H NMR (300 MHz, CDCl3) δ ppm 8.50 (dd, 1H, J1=5.1 Hz, J2=1.8 Hz), 7.89 (dd, 1H, J1=7.5 Hz, J2=1.5 Hz), 7.69 (dd, 2H, J1=8.4 Hz, J2=1.2 Hz), 7.46-7.40 (m, 1H), 7.27-7.13 (m, 5H), 7.01-6.89 (m, 2H), 6.85-6.80 (m, 1H), 6.53 (s, 1H), 6.14 (d, 1H J=10.2 Hz), 2.71-2.59 (m, 1H), 1.15-1.10 (m, 6H).

Provenance & Evidence