Dichloromethane → HCID 136387211, compound

Participants

Reaction Conditions

Reaction Steps

To a vial containing 3-bromo-5-nitro-1-trityl-1H-indazole (1.45 g, 3.00 mmol), 4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE (0.873 g, 4.50 mmol) [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (0.245 g, 0.300 mmol) and Potassium phosphate (1.59 g, 7.50 mmol) in a mixture of 1,4-Dioxane (25 mL, 320 mmol) Water (12 mL, 670 mmol) was degassed under an atmosphere of Nitrogen. This r×n mixture was heated at 80° C. overnight under an atmosphere of Nitrogen. TLC (20% EtOAc/hexane) showed starting material. MS showed (M+H) at 472. The r×n was diluted with EtOAc and Water (50/50 mL) and filtered through Celite. The org. layer was washed with water, dried over Magnesium sulfate (2 g, 20 mmol) and rotavap to give a crude, 2.2 g. The crude was chrom. (30% EtOAc/Hexane) on Biotage (40 L) to obtain the product (fraction 2), M+H at 472, 5-nitro-3-(1H-pyrazol-4-yl)-1-trityl-1H-indazole (0.54 g; Yield=38%)

Provenance & Evidence