Water → HCID 21110080, compound

Participants

Reaction Conditions

Reaction Steps

5.5 g (31 mmol) of 4-chloro-2-methylquinoline and 8.9 g (65 mmol) of potassium carbonate were added to 4.6 g (26 mmol) of methyl 1H-pyrrolo[2,3-b]pyridine-3-carboxylate in 93 cm3 of dimethyl sulfoxide under argon. The reaction mixture was heated at a temperature in the region of 120° C. for 16 h, then it was cooled to a temperature in the region of 20° C. and treated with 250 cm3 of water. The aqueous phase was extracted with 250 cm3 and then 125 cm3 of ethyl acetate. The organic extracts were combined, dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2.7 kPa). The residue was purified by flash chromatography on a column of silica gel (0.04–0.06 mm), elution being carried out with dichloromethane. The fractions comprising the expected product were combined and then concentrated to dryness under reduced pressure (2.7 kPa). 1.4 g of methyl 1-(2-methylquinolin-4-yl)-1H-pyrrolo[2,3-b]pyridine-3-carboxylate were thus obtained in the form of an orange crystalline solid melting at 179° C.

Provenance & Evidence