Potassium Carbonate → methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate

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Reaction Steps

Methyl (2Z)-2-{[(benzyloxy)carbonyl]amino}-3-(2-chloro-4-iodopyridin-3-yl)prop-2-enoate (11.46 g, 24.25 mmole), K2CO3 (10.05 g, 72.7 mmole), CuI (0.462 g, 2.425 mmole), and L-proline (0.558 g, 4.85 mmole) were combined in 1,4-dioxane (120 mL). The mixture was degassed (3× pump/N2) then heated to reflux. After stirring at reflux overnight the mixture was cooled to RT, diluted with saturated aqueous NH4Cl, and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered through a pad of Celite, and concentrated. The resulting solid was triturated with Et2O/hexanes to give the title compound (4.6 g, 90%) as an off-white solid. NMR (399 MHz, CDCl3): δ 9.25 (s, 1 H); 8.18 (d, J=5.8 Hz, 1 H); 7.35 (d, J=2.1 Hz, 1 H); 7.29 (d, J=5.9 Hz, 1 H); 3.99 (s, 3 H).

Provenance & Evidence