Cesium carbonate → Methyl 3-hexylquinoline-8-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(((trifluoromethyl)sulfonyl)oxy)quinoline-8-carboxylate (538 mg, 1.6 mmol), hexylboronic acid (415 mg, 3.2 mmol) and Cs2CO3 (779 mg, 2.4 mmol) were suspended in toluene (30 mL). The mixture was purged with nitrogen then tetrakis(triphenylphosphine)palladium (0) (55 mg, 0.05 mmol) was added. The reaction was sealed and heated at 95° C. for 16 h. The mixture was cooled and filtered through celite, rinsing with excess CH2Cl2. The filtrate was concentrated in vacuo. The resulting oil was purified on 40 g silica gel (19:1 CH2Cl2/methyl t-butyl ether) to afford 178 mg (41%) of methyl 3-hexylquinoline-8-carboxylate.

Provenance & Evidence