Potassium Fluoride → methyl 4-(3-methoxyphenyl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

Intermediate A1, Methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (500 mg, 2.374 mmole), 3-methoxyphenylboronic acid (469 mg, 3.09 mmole), Pd(OAc)2 (32.0 mg, 0.142 mmole), X-Phos (113 mg, 0.237 mmole), and KF (414 mg, 7.12 mmole) were combined in 1,4-dioxane (10 mL). The mixture was degassed (3× pump/N2) then heated to 100° C. After 2 hr the mixture was cooled to RT, diluted with EtOAc, filtered through a pad of Celite washing with EtOAc, and concentrated. Flash column (Biotage-SNAP-50 g SiO2, 50% EtOAc/hexanes) gave the title compound (574 mg, 86%) as an off-white solid. 1H NMR (399 MHz, CDCl3): δ 9.26 (bs, 1 H); 8.51 (d, J=5.8 Hz, 1 H); 7.58-7.51 (m, 3 H); 7.50-7.40 (m, 1 H); 7.30 (d, J=5.9 Hz, 1 H); 7.03 (dd, J=8.2, 2.6 Hz, 1 H); 3.97 (s, 3 H); 3.91 (s, 3 H).

Provenance & Evidence