HCID 66650463, compound → HCID 59154135, compound

Participants

Reaction Conditions

Reaction Steps

Compound 137 (5.5 g) was dissolved in dichloroethane (1.375 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. At 45 min, 2-mercaptonicotinic acid (0.5 eq.) was added. The reaction mixture was cooled down to room temperature, concentrated under vacuum to ˜130 mL, and then washed with 0.5M aqueous NaHCO3. To the separated organic phase was added MNA (0.5 eq.) 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 (5.5 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 crystallized from hot methanol and DCE to give compound 62d (2.87 g) as a white solid in 54% yield and 98% purity. More product was obtained similarly from the filtrate to give 487 mg of a white solid. Thus, the total yield was 63%.

Provenance & Evidence