反应详情

温度

120 °C

To a cold (0° C.), stirred solution of 0.82 mL of allyl alcohol in 12 mL of dry THF, under argon, is added 2.1 mL of a 2.5 M solution of butyllithium in hexanes. The solution is stirred for 5 min, then added via cannula to a cold (0° C.), stirred mixture of 1.25 g of ethyl 3-(bromomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 19) in 8 mL of dry DMF. The resulting solution is stirred at 0° C. for 20 min, then quenched with dil. HCl. Aqueous workup (EtOAc/dil HCl) followed by flash chromatography on silica using 3% MeOH in CH2Cl2 affords a mixture of ethyl and allyl esters (873 mg). A mixture of 165 mg of the mixed esters and 580 mg of p-chlorobenzylamine is heated at 120° C. for 18 h, then cooled and diluted with ether. The resulting solid is filtered, washed well with ether, and dried in vacuo. Flash chromatography of the solid on silica using 2% MeOH in CH2Cl2 provides 922 mg of the title compound as a pale yellow solid. Recrystallization from EtOAc affords glistening yellow prisms.

1. additionadded via cannula to a cold (0° C.)
2. stirringstirred
3. stirringThe resulting solution is stirred at 0° C. for 20 min
4. customquenched with dil. HCl
5. customaffords
6. temperaturecooled
7. filtrationThe resulting solid is filtered
8. washwashed well with ether
9. customdried in vacuo