HCID 57816684, compound → HCID 44230108, compound

Participants

Reaction Conditions

Reaction Steps

Compound 129 (3.91 g) was dissolved in dichloroethane (980 mL) under Ar at room temperature. The solution was degassed with argon and then heated at 73-77° C. Zhan 1B catalyst (1%) in dichloroethane was slowly added to the reaction solution. At 25 min, another 1% of the catalyst in DCE was added. In total, 8% of the catalyst was added over 4 hrs and 20 min. The reaction mixture was treated with 2-mercaptonicotinic acid (“MNA”) (1 g). The reaction mixture was cooled down to room temperature, concentrated under vacuum to ˜100 mL, and then washed with 0.5M aqueous NaHCO3. To the separated organic phase was added MNA (1 g) and the mixture was stirred at room temperature for 55-65 min. The mixture was washed twice with aqueous 0.5M NaHCO3, dried over Na2SO4, and filtered. Charcoal (11 g) was added to the organic solution and the mixture was stirred at room temperature for 15 hrs. The mixture was concentrated under vacuum to ˜10-15 mL and filtered through a silica plug. The crude solid was triturated in warm methanol to give compound 68b (1.1 g) as an off-white solid in 30% yield and 98% purity.

Provenance & Evidence