Diisopropylethylamine → 5-Formyl-4'-methyl-N-((6-methylpyridin-3-yl)methyl)biphenyl-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Into a round bottom flask were combined 5-formyl-4′-methylbiphenyl-3-carboxylic acid (3.00 g, 12.5 mmol), (6-methylpyridin-3-yl)methanamine (1.91 g, 15.6 mmol), N,N-diisopropylethylamine (6.46 g, 49.9 mmol) and N,N-dimethylformamide (97 mL). N,N,N′,N′-Tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (9.50 g, 25.0 mmol) was added in one portion and the mixture was heated at 60° C. for 2 h. After cooling, the mixture was poured onto saturated sodium bicarbonate (200 mL) and extracted with ethyl acetate (3×100 mL). The combined extracts were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using methylene chloride:methanol gradient (0-10%) to afford the title compound. LC-MS: 346.2 [M+1]+; 1H NMR (400 MHz, DMSO-d6): 10.14 (s, 1H), 8.46-8.43 (m, 2H), 8.37-8.33 (m, 2H), 7.72 (d, 2H, J=8.0 Hz), 7.64 (dd, 1H, J=8.0 Hz), 7.34 (d, 2H, J=7.9 Hz), 7.22 (d, 2H, J=7.9 Hz), 4.51 (d, 2H, J=5.9 Hz), 2.44 (s, 3H), 2.37 (s, 3H).

Provenance & Evidence