Tetrabutylammonium Fluoride → HCID 136016210, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[1-tert-butoxycarbonyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-1H-thieno[3,2-c]pyrazol-3-yl]-6-(tert-butyl-dimethyl-silanyloxy)-indole-1-carboxylic acid tert-butyl ester [3.2 g, 4.5 mmol, Intermediate (75)] in tetrahydrofuran (30 mL) at 0° C. was added a 1.0 M TBAF solution in tetrahydrofuran. The green solution was stirred at 0° C. until the reaction is complete and was then diluted with water. The resulting mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was chromatographed through silica gel (dichloromethane/ethyl acetate, 90/10 as eluant) to produce 2-(1-tert-butoxycarbonyl-5-hydroxymethyl-1H-thieno[3,2-c]pyrazol-3-yl)-6-hydroxy-indole-1-carboxylic acid tert-butyl ester [1.5 g (66%, Intermediate (76)]. LC/MS: 486.2 (M+H), RT=3.30 minutes.

Provenance & Evidence