3-Hydroxypyridine → HCID 51037724, compound

Participants

Reaction Conditions

Reaction Steps

Compound 1 (50 mg, 0.19 mmol, 1.0 eq), 3-hydroxypyridine (26.7 mg, 0.281 mmol, 1.50 eq), CuI (3.7 mg, 0.019 mmol, 0.10 eq), Cs2CO3 (122 mg, 0.374 mmol, 2.00 eq) and N,N-dimethylglycine hydrochloride (7.8 mg, 0.056 mmol, 0.30 eq) were dissolved in 1,4-dioxane (1 mL) in a flame-dried sealed tube and heated overnight at 90° C. The reaction was cooled to rt, plugged through celite and concentrated. Purification by flash chromatography on silica gel afforded 24 mg (40%) of the title compound as a pale yellow oil: 1H NMR (400 MHz, DMSO-d6) δ 11.06 (s, 1H), 8.55-8.53 (m, 2H), 8.31 (d, J=5.7 Hz, 1H), 8.01 (m, 1H), 7.92 (d, J=7.8 Hz, 1H), 7.79 (d, J=2.3 Hz, 1H), 7.73 (ddd, J=8.4, 2.6, 1.2 Hz, 1H), 7.64 (d, J=8.6 Hz, 1H), 7.55 (dd, J=8.4, 4.7 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H) 6.82, (dd, J=5.7, 2.4 Hz, 1H); ES-MS [M+1]+: 326.1.

Provenance & Evidence