반응 #1144281

반응 방정식

5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Intermediate 1

5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

trimethylsilylacetylene

→

crude product

1-(Tetrahydro-2H-pyran-2-yl)-5-((trimethylsilyl)ethynyl)-1H-indazole

용매

THF triethylamine

반응 조건

후처리

1. 1
   기타This mixture was degassed with three vacuum/N2 cycles
2. 2
   기타The pressure tube was sealed
3. 3
   온도Upon completion by LCMS, the reaction mixture was cooled down to room temperature
4. 4
   여과filtered through Celite with ethyl acetate (200 mL)
5. 5
   농축The filtrate was concentrated

실험 절차

To a 250-mL pressure tube, 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (11.9 g, 42.3 mmol; Intermediate 1), Pd(Ph3P)2Cl2 (1.48 g, 0.05 mmol), CuI (0.8 g, 4.2 mmol) and THF/triethylamine (5:1, 85 mL) were added. This mixture was degassed with three vacuum/N2 cycles, and then trimethylsilylacetylene (9 mL, 63.5 mmol) was added. The pressure tube was sealed and heated at 80° C. for 2 days. Upon completion by LCMS, the reaction mixture was cooled down to room temperature and filtered through Celite with ethyl acetate (200 mL). The filtrate was concentrated to give the crude product that was used directly in the next step. LCMS: 299 (M+H)+.

출처