反应详情

A mixture of 2-iodo-5-methoxy-N-trifloroacetylaniline (Flynn et al, J. Med. Chem., 2002, 45(12), 2670; 0.508 g; 1.5 mmol), Cl2Pd(PPh3)2 (0.102 g; 0.145 mmol); CuI (0.016 g; 0.085 mmol), anhydrous N,N-diisopropyl ethylamine (1 ml) in anhydrous DMF (10 ml) was cooled to −40° C., degassed under reduced pressure and saturated with dry N2. The propyne gas (0.53 g; 13.3 mmol) was added to it at −40° C. The reaction flask was sealed with septum and allowed to warm up to room temperature and stirred for 3 h. After removal of excess of propyne under reduced pressure 3,4,5-trimethoxyphenyl iodide (0.5 g; 1.7 mmol) was added to it, followed by dry K2CO3 (0.621 g; 4.5 mmol). The resulting mixture was degassed in vacuo and saturated with CO gas and stirred for 3 h under CO balloon pressure. The mixture was diluted to 50 ml with diethyl ether, washed with H2O (2×15 ml), brine (10 ml), dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2; CH2Cl2) to give pure title compound (0.295 g; 55%) as a yellow crystals:

1. customdegassed under reduced pressure and saturated with dry N2
2. customThe reaction flask was sealed with septum
3. additionwas added to it
4. customThe resulting mixture was degassed in vacuo and saturated with CO gas
5. stirringstirred for 3 h under CO balloon pressure
6. additionThe mixture was diluted to 50 ml with diethyl ether
7. washwashed with H2O (2×15 ml), brine (10 ml)
8. dry with materialdried over anhydrous MgSO4
9. filtrationfiltered
10. customfiltrate evaporated to dryness under reduced pressure
11. customThe residue was purified by flash column chromatography (SiO2; CH2Cl2)