反应详情

温度

100 °C

N-(5-iodo-4-methyl-1,3-thiazol-2-yl)acetamide, Intermediate 1 (2 g; 7.09 mmol; 1 eq.) and Pd(dppf)Cl2 (0.52 g; 0.71 mmol; 0.10 eq.) are dissolved in DMF (35 ml). 2-(Tributylstannyl)thiophene (2.68 ml; 8.44 mmol; 1.19 eq.) is added. The reaction mixture is flushed with argon and heated at 100° C. for 1 h 30. Solvents are evaporated and the crude mixture is dissolved in EtOAc (100 ml), washed with water (3×100 ml). The aqueous phase are combined and extracted with EtOAc (2×50 ml). Combined organic phases is washed with brine and dried over MgSO4. After evaporation of the solvents, the crude product is purified by preparative HPLC, affording N-[4-methyl-5-(2-thienyl)-1,3-thiazol-2-yl]acetamide as white-off powder (1.24 g; 73.5%). 1H NMR (DMSO-d6) δ 2.16 (s, 3H), 2.42 (s, 3H), 7.15 (dd, J=3.8, 5.3 Hz, 1H), 7.20 (dd, J=1.1, 3.8 Hz, 1H), 7.60 (dd, J=1.1, 5.3 Hz, 1H), 12.19 (s, 1H). M− (ESI): 237.01; M+ (ESI): 239.01. HPLC, Rt: 3.01 min (purity: 98.7%).

1. customThe reaction mixture is flushed with argon
2. customSolvents are evaporated
3. dissolutionthe crude mixture is dissolved in EtOAc (100 ml)
4. washwashed with water (3×100 ml)
5. extractionextracted with EtOAc (2×50 ml)
6. washCombined organic phases is washed with brine
7. dry with materialdried over MgSO4
8. customAfter evaporation of the solvents
9. customthe crude product is purified by preparative HPLC