2-Chloropyridine → HCID 58580251, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-4-(hydroxymethyl)pyridin-2(1H)-one Part B (50 mg, 0.16 mmol) and 2-chloropyridine (0.059 mL, 0.63 mmol) in DMF (0.6 mL) was added to a mixture of Pd(OAc)2 (7.0 mg, 0.03 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (19 mg, 0.05 mmol), and Cs2CO3 (128 mg, 0.39 mmol) in 0.4 ml DMF. The mixture was stirred 15 min prior to heating at 80° C. for 6 h. After cooling to RT, the mixture was diluted with EtOAc and was filtered. The filtrate was concentrated and the residue was purified by Prep-HPLC (MeOH/H2O/TFA) to afford the title compound A-4 as a white solid (24 mg, 37% yield). LC-MS, [M+H]+=397. 1H NMR (CDCl3, 400 MHz) δ 8.16 (m, 1H), 7.62 (m, 1H), 7.31 (d, J=7.1 Hz, 1H), 6.91 (m, 5H), 6.72 (s, 1H), 6.28 (dd, J=7.1 and 2.2 Hz, 1H), 5.29 (s, 2H), 3.85 (s, 5H), 1.33 (s, 6H), HPLC-Method 6; 3.07 min.

Provenance & Evidence