Sodium Carbonate → HCID 53235215, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-bromo-2-(5-isopropyl-[1,2,4]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene (84 mg, 0.21 mmol), 4,4,5,5-tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (62 mg, 0.32 mmol), tetrakis(triphenylphosphine) palladium (0) (24 mg, 0.021 mmol) and sodium carbonate (45 mg, 0.42 mmol) in acetonitrile (6 mL) and water (3 mL) under nitrogen was heated at 140° C. for 25 mins under microwave irradiation. More tetrakis(triphenylphosphine) palladium (0) (24 mg, 0.021 mmol) was added, and heating was pursued for 30 mins at 150° C. The reaction mixture was diluted with ethyl acetate and water. The organic layer was washed with brine, dried (Na2SO4), concentrated in vacuo and purified twice by flash chromatography (SiO2, gradient 50 to 75% ethyl acetate in cyclohexane, then 60% ethyl acetate in cyclohexane) to afford 484 as an off-white solid (16 mg, 20%). LCMS (Method C): RT=10.30 min, [M+H]+=379. 1H NMR (DMSO-d6): 12.98 (1 H, bs), 8.28 (1 H, bs), 8.18 (1 H, d, J=8.3 Hz), 8.16 (1 H, s), 7.99 (1 H, bs), 7.46 (1 H, dd, J=8.3, 1.8 Hz), 7.34 (1 H, d, J=1.8 Hz), 4.38 (2 H, t, J=5.0 Hz), 4.13-4.01 (1 H, m), 3.37 (2 H, t, J=5.0 Hz), 1.43 (3 H, s), 1.41 (3 H, s).

Provenance & Evidence