反应详情

1,4-Dichlorophthalazine (1.40 g, 7.03 mmol), 4-methylthiophen-2-ylboronic acid (999 mg, 7.03 mmol), and PdCl2(DPPF)(721 mg, 985 μmol) were added into a sealed tube. The tube was purged with Argon. Then sodium carbonate (2.0 M in water)(7.74 ml, 15.5 mmol) and 1,4-dioxane (35.2 ml, 7.03 mmol) were added. The tube was sealed, stirred at RT for 5 min, and placed in a preheated oil bath at 110° C. After 1 h, LC-MS showed product and byproduct (double coupling), and SM dichlorophthalazine. The reaction was cooled to RT, filtered through a pad of celite with an aid of EtOAc, concentrated, and loaded onto column. The product was purified by column chromatography using Hex to remove the top spot, then 80:20 Hex:EtOAc to collect the product. The product, 1-chloro-4-(4-methylthiophen-2-yl)phthalazine was obtained as yellow solid. LC-MS showed that the product was contaminated with a small amount of SM dichlorophthalazine and biscoupling byproduct. MS m/z=261 [M+1]+. Calcd for C13H9ClN2S: 260.12.

1. customThe tube was purged with Argon
2. customThe tube was sealed
3. customplaced in a preheated oil bath at 110° C
4. waitAfter 1 h
5. temperatureThe reaction was cooled to RT
6. filtrationfiltered through a pad of celite with an aid of EtOAc
7. concentrationconcentrated
8. customThe product was purified by column chromatography
9. customto remove the top spot
10. custom80:20 Hex:EtOAc to collect the product