Sodium Carbonate → HCID 59384371, compound

Participants

Reaction Conditions

Reaction Steps

The suspension of 4,4,5,5-tetramethyl-2-(4-(octyloxy)-3-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 3a (136 mg, 0.34 mmol, 1.5 equiv), diethyl 2-(5-bromopyridin-2-yl)-2-(tert-butoxycarbonylamino)malonate (98 mg, 0.23 mmol, 1.0 equiv), Pd(PPh3)4 (26.3 mg, 0.023 mmol, 0.1 equiv), and Na2CO3 (120 mg, 1.14 mmol, 4.0 equiv) in ethanol-H2O was heated at 80° C. for 1 hour. The reaction mixture was filtered and the filtrate was purified by silica gel column to afford the title compound in 77% (110 mg) yield. MS (ESI, M+H+)=625.1; 1H NMR (400 MHz, CDCl3) δ 8.66 (s, 1H), 7.88 (s, 1H), 7.86 (dd, 1H, J=8.4 Hz, J=2.0 Hz), 7.75 (d, J=2.5 Hz), 7.66 (d, 1H, J=8.4 Hz), 7.08 (d, 1H, J=8.4 Hz), 6.82 (s, 1H), 4.30 (m, 4H), 4.09 (t, 2H, J=6.0 Hz), 1.84 (m, 2H), 1.46 (m, 11H), 1.28 (m, 14H), 0.90 (t, 3H, J=7.2 Hz).

Provenance & Evidence