methylpyrrolidine 2 carbaldehyde 10e 1 g yield 56 8 as a brown oil n 4 3 chloro 4 2 pyridylmethoxy phenyl amino 3 cyano 7 ethoxy 6 quinolyl 2 diethoxyphosphoryl acetamide 1d 3 g 4 40 mmol was dissolved in 30 ml of tetrahydrofuran in a dry ice bath followed by dropwise addition of a solution of lithium bis trimethylsilyl amide 1 m in toluene 9 6 ml 8 80 mmol after the mixture was stirred for 30 minutes a solution of 1 methylpyrrolidine 2 carbaldehyde 10e 1 g 8 80 mmol in 5 ml of tetrahydrofuran was added dropwise the reaction mixture was stirred for another 30 minutes then warmed up to room temperature and stirred for 24 hours the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography with elution system a to obtain the title compound e n 4 3 chloro 4 2 pyridylmethoxy phenyl amino 3 cyano 7 ethoxy 6 quinolyl 3 1 methylpyrrolidin 2 yl prop 2 enamide 10 500 mg yield 20 8 as a yellow solid 1 h nmr 400 mhz dmso d 6 u03b4 11 59 s 1h 11 28 s 1h 9 19 s 1h 9 05 s 1h 8 71 d 1h 8 09 8 07 m 1h 7 74 7 68 m 3h 7 56 7 55 m 1h 7 45 7 37 m 2h 7 04 7 00 m 1h 6 88 6 84 m 1h 5 43 s 2h 4 38 dd 2h 4 10 m 2h 3 63.