Water → 6-amino-5-ethynyl-1H-indazole-7-carboxylic acid methyl ester

Participants

Reaction Steps

To a solution of 500 mg (1.74 mmol) of 6-amino-5-trimethylsilanylethynyl-1H-indazole-7-carboxylic acid methyl ester in 17 mL of anhydrous tetrahydrofuran under an atmosphere of argon is added 2.6 mL (2.6 mmol) of a 1 M solution tetrabutylamonium fluoride in tetrahydrofuran. The reaction mixture is stirred at ambient temperature for 2 hours. Water and tert-butylmethylether are added and the two phases are separated. The aqueous layer is extracted with tert-butylmethylether. The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The residue is suspended in hexanes. Filtration affords 210 mg (56%) of the product as a yellowish solid; LC/MS:216/217 (M+H)+.

Provenance & Evidence