Sodium Carbonate → HCID 21198039, compound

Participants

Reaction Steps

A mixture of 2.5 gm (14.5 mMol) isoquinolin-4-ylboronic acid, 3.43 gm (10.3 mMol) 1-tert-butoxy-carbonyl-4-trifluoromethanesulfonyloxy-1,2,5,6-tetrahydropyridine, 1.3 gm (30.9 mMol) lithium chloride, 0.04 gm (0.05 mMol) [1,1′-bis (diphenylphosphino)-1-ferrocene]-palladium II chloride, and 2 mL 2M aqueous sodium carbonate in about 20 mL tetrahydrofuran containing a few drops of methanol was stirred at reflux for about 4 hours. The reaction was cooled to room temperature and then partitioned between ethyl acetate and 2N sodium hydroxide. The phases were separated and the aqueous phase was extracted well with ethyl acetate. The organic phases were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with 3:2 hexane:ethyl acetate. Fractions containing product were combined and concentrated under reduced pressure to provide 0.216 gm (57%) 1-tert-butoxycarbonyl-4-(isoquinolin-4-yl)-1,2,5,6-tetrahydropyridine as a light yellow oil.

Provenance & Evidence