Sodium hydride → Methyl 4-chloro-1-[(5-phenyl-1,2,4-oxadiazol-3-yl)methyl]-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

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Reaction Steps

To a solution of methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate (500 mg, 2.374 mmole) in DMF (10 mL) was added NaH (60% dispersion in mineral oil, 123 mg, 3.09 mmole) portionwise at RT. After 30 min 3-(chloromethyl)-5-phenyl-1,2,4-oxadiazole (601 mg, 3.09 mmole) was added all at once as a solid. After 6 hr the mixture was diluted with saturated aqueous NH4Cl and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column chromatography (Biotage-SNAP-25 g SiO2, O-20% EtOAc/hexanes) gave the title compound (553 mg, 63%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.21 (d, J=6.0 Hz, 1 H); 8.05 (dd, J=7.8, 1.5 Hz, 2 H); 7.59-7.54 (m, 1 H); 7.54-7.44 (m, 3 H); 7.39-7.35 (m, 1 H); 6.03 (s, 2 H); 3.97 (s, 3 H).

Provenance & Evidence