Trifluoroacetic acid → HCID 58405983, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoropyridine-3-boronic acid (26.9 mg), tetrakis(triphenylphosphine)palladium (11.0 mg) and a 1 N sodium carbonate solution (191 μl) were sequentially added to a solution of (±)-N,N-di-(tert-butyloxycarbonyl)-[(4aR*,8aS*)-8a-(4-bromothiophen-2-yl)-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]amine obtained in Preparation Example 19-(3) (51.0 mg) in DMF (2.0 ml). After replacement with nitrogen, the mixture was stirred at 80° C. for five hours. The reaction solution was returned to room temperature and diluted with water. The aqueous layer was extracted with ethyl acetate, and the organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain an intermediate. The resulting intermediate was dissolved in dichloromethane (5.0 ml). TFA (2.0 ml) was added and the mixture was stirred at room temperature for three hours. Ice was added to the mixture, followed by neutralization with a sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-silica gel column chromatography to obtain the title compound (22.0 mg).

Provenance & Evidence