2-Methylpentane → HCID 68902777, compound

Participants

Reaction Steps

A mixture of 2-bromo-5-fluoropyridine (38 mg, 0.22 mmol), (1S)-1-(2-{[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]sulfonyl}phenyl)ethanol (96 mg, 0.22 mmol), palladium(II) acetate (2.6 mg, 11 μmol), tri(o-tolyl)phosphine (5.2 mg, 17 μmol) and sodium carbonate (51 mg, 0.48 mmol) in DME (2 mL) and water (0.3 mL) was degassed by bubbling nitrogen through for 5 minutes, then was heated at reflux under nitrogen for 3 hours. The slurry was filtered, and the filtrate was washed with saturated sodium hydrogen carbonate solution (10 mL), with saturated sodium chloride solution (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel, eluting with 40% ethyl acetate in isohexane, then further purified by preparative TLC on silica gel, eluting with 50% ethyl acetate in isohexane. The product was isolated as a colourless solid, which solidified upon trituration with isohexane (13 mg, 15%). 1H NMR (400 MHz, CDCl3): δ 8.61 (1H, d, J=2.7 Hz), 8.55 (1H, s), 8.48 (1H, s), 8.21 (2H, dd, J=8.7, 21.9 Hz), 8.06 (2H, dd, J=8.7, 22.5 Hz), 7.90 (1H, dd, J=4.1, 8.7 Hz), 7.77 (2H, d, J=7.6 Hz), 7.66 (1H, t, J=7.5 Hz), 7.57-7.49 (2H, m), 5.65 (1H, m), 2.48 (1H, s), 1.34 (3H, d, J=6.4 Hz). m/z (ES+) 408 [MH+].

Provenance & Evidence