8-Hydroxyquinoline → HCID 56941125, compound

Participants

Reaction Conditions

Reaction Steps

2,5-dihydro-1H-pyrido[4,3-b]indol-1-one (I-62a: 500 mg, 2.71 mmol), 3-iodo-4-methylpyridine (892 mg, 4 mmol), 8-hydroxy quinoline (79 mg, 0.542 mmol) and K2CO3 (560 mg, 4.06 mmol) were added to a previously degassed solution of DMSO (10 mL). This was followed by the addition of CuI (103.2 mg, 0.542 mmol) and the resulting reaction mass was heated at 150° C. for 16 hours in a sealed tube. The reaction was monitored by TLC (5% methanol in DCM). The reaction mass was quenched with water, diluted using ethyl acetate and filtered. The filtrate was extracted using ethyl acetate, washed the organic layer with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (1% methanol in DCM), followed by preparative HPLC afforded 40 mg of the product (5.4% yield).

Provenance & Evidence