Cesium fluoride → Methyl 4-[4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]pyridine-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of the [4-methoxy-3-(3,3,6,6-tetramethyl-1,8-dioxo-2,3,4,5,6,7,8,9-octahydro-1H-xanthen-9-yl)phenyl]boronic acid produced in Example 1-1 (511 mg, 1.20 mmol), methyl 4-chloropyridine-2-carboxylate (207 mg, 1.20 mmol), tri(o-tolyl)phosphine (73.3 mg, 0.24 mmol), cesium fluoride (548 mg, 3.61 mmol), and palladium(II) acetate (13.5 mg, 0.06 mol) in 1,2-dimethoxyethane (10.2 ml) was prepared at room temperature, and the suspension thus prepared was then stirred at 90° C. for 7 hours. After air-cooling, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure, and the residue thus obtained was then purified by silica gel column chromatography (ethyl acetate:hexane=34:66 to 25:75, v/v) to obtain the title compound (123 mg, yield: 20%).

Provenance & Evidence