Potassium Carbonate → 6'-(3,6-Dihydro-2H-pyran-4-yl)-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

Participants

Reaction Conditions

Reaction Steps

A mixture of 6′-bromo-4-methyl-3′-nitro-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl (as prepared in Example 61, step (a)) (237 mg, 0.79 mmol), anhydrous K2CO3 (311 mg, 2.25 mmol) and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (Murata, M., Synthesis, 778, (2000)) (157 mg, 0.750 mmol) in dioxane (5 mL) was heated at 80° C. overnight under Ar. The reaction mixture was allowed to cool to RT, concentrated and the resulting residue was purified on silica (10% EtOAc/hexane) to obtain the expected coupled compound (71 mg, 30%). 1H-NMR (CDCl3; 400 MHz): δ 8.15 (d, 1H, J=8.4 Hz), 6.80 (m, 2H), 4.39 (m, 2H), 3.92 (t, 2H, J=5.4 Hz), 3.76 (m, 2H), 3.04 (m, 2H), 2.62 (m, 2H), 1.67 (m, 3H), 1.33 (m, 2H), 0.99 (d, 3H, J=6.3 Hz).

Provenance & Evidence