Sodium hydride → Methyl 1-[2-(4-chlorophenoxy)ethyl]-4-(2-fluoropyridin-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

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To a solution of methyl 4-(2-fluoropyridin-4-yl)-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (67 mg, 0.247 mmole) in DMF (1.2 mL) was added NaH (60% dispersion in mineral oil, 13 mg, 0.325 mmole) at RT. After gas evolution had ceased 1-(2-bromoethoxy)-4-chlorobenzene (76 mg, 0.321 mmole) was added and the mixture was heated to 60° C. After 3 hr the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-10 g SiO2, 35% EtOAc/hexanes) gave the title compound (86 mg, 82%) as a white foam. 1H NMR (400 MHz, CDCl3): δ 8.58 (d, J=5.9 Hz, 1 H); 8.39 (d, J=5.2 Hz, 1 H); 7.79 (d, J=5.4 Hz, 1 H); 7.60-7.51 (m, 3 H); 7.18-7.15 (m, 2 H); 6.72-6.67 (m, 2 H); 5.02-4.96 (m, 2 H); 4.39-4.33 (m, 2 H); 3.97 (s, 3 H).

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