Sodium Carbonate → HCID 21099406, compound

Participants

Reaction Conditions

Reaction Steps

2-Vinyl-5-[(2-fluorophenyl)sulfonyl]pyridine (Example 6 Step 1; 50 mg, 0.19 mmol), 2,4-difluorophenylboronic acid (75 mg, 0.475 mmol), chloro(1,5-cyclooctadiene)rhodium(I) dimer (2 mg, 0.004 mmol) and sodium carbonate (40 mg, 0.377 mmol) were taken up in water (1 mL) and heated in a microwave reactor at 150° C. for 10 minutes. The dark suspension was diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried over MgSO4 and concentrated while loading onto silica. Eluting through a plug of silica using 20% ethyl acetate/isohexane followed by mass-triggered preparative HPLC gave the title compound as a pale yellow solid (10 mg, 14%). δH (500 MHz, d6 DMSO): 8.99 (1H, s), 8.21 (1H, dd, J=1.8, 8.3 Hz), 8.06 (1H, td, J=1.6, 7.6 Hz), 7.84-7.78 (1H, m), 7.52-7.48 (2H, m), 7.43 (1H, t, J=9.5 Hz), 7.28 (1H, q, J=8.0 Hz), 7.11 (1H, td, J=2.4, 9.9 Hz), 6.94 (1H, td, J=2.1, 8.5 Hz), 3.12-3.10 (2H, m), 3.01-2.98 (2H, m); m/z (ES+) 378 [MH+].

Provenance & Evidence