反应详情

温度

70 °C

A solution of methyl 5-(S-methylsulfonimidoyl)pentanoate (2.32 g) was dissolved in anhydrous DMF (30 mL) and to this solution was added 5-iodo-6-amino-nicotinic acid (3.17 g, ˜1 eq), diisopropylethylamine (4.2 mL, 2 eq), and BOP (5.85 g, 1.1 eq). The reaction mixture was heated at 70° C. for 1 hour and then partitioned between EtOAc and aq NH4Cl. The organic layer was separated, washed sequentially with aq NH4Cl (1×), saturated aq NaHCO3 (1×), brine (1×), and dried with anhydrous Na2SO4 overnight. The upper solution layer was decanted, concentrated, and the brown oily reside was subject to column chromatography (acetone-CHCl3 1:100 to MeOH-acetone-CHCl3 1:2:50). Concentration of the product eluting fractions provided the title compound as a slight yellow colored foam (2.65 g).

1. custompartitioned between EtOAc and aq NH4Cl
2. customThe organic layer was separated
3. washwashed sequentially with aq NH4Cl (1×), saturated aq NaHCO3 (1×), brine (1×)
4. dry with materialdried with anhydrous Na2SO4 overnight
5. customThe upper solution layer was decanted
6. concentrationconcentrated
7. washConcentration of the product eluting fractions