Dimethylamine → HCID 24800869, compound

Participants

Reaction Steps

Methyl 6-(2-(3-(4′-formylbiphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate (19 mg, 0.043 mmol) and dimethylamine (2 M in THF, 0.026 mL, 0.052 mmol) were dissolved in dichloroethane (2 mL) and NaBH(OAc)3 (16 mg, 0.078 mmol) was added. The reaction solution was stirred under an atmosphere of Ar at ambient temperature for 2 h and then quenched with saturated aqueous NaHCO3. The crude product was extracted with EtOAc and the solvent was removed in vacuo. The crude product was purified with preparative thin layer chromatography (SiO2, 5% Et3N, 5% MeOH, 90% EtOAc) to furnish methyl 6-(2-(3-(4′-((dimethylamino)methyl)biphenyl-4-yl)propanoyl)oxazol-5-yl)pyridine-2-carboxylate as a tan solid (5 mg, 25%): 1H NMR (CDCl3, 600 MHz) δ 8.12 (d, 1H, J=7.7 Hz), 8.03 (d, 2H, J=9.6 Hz), 7.97 (t, 1H, J=7.8 Hz), 7.53 (dd, 4H, J=8.0, 4.9 Hz), 7.38 (d, 2H, J=7.9 Hz), 7.34 (d, 2H, J=8.0 Hz), 4.03 (s, 3H), 3.51 (t, 4H, J=7.6 Hz), 3.15 (t, 2H, J=7.6 Hz), 2.31 (s, 6H); 13C NMR (CDCl3, 150 MHz) δ 187.3, 165.1, 157.4, 152.4, 148.5, 146.5, 139.4, 138.9, 138.3, 129.6, 128.9, 128.0, 127.2, 126.9, 125.2, 123.3, 63.8, 53.1, 45.1, 40.6, 29.3; HR ESI-TOF m/z 470.2071 (M+H+, C28H27N3O4, requires 470.2074).

Provenance & Evidence