Short-RInChIKey=SA-FUHFF-UHFFFADPSC-KIQBPEXSAZ-UHFFFADPSC-NUHFF-NUHFF-NUHFF-ZZZ

The pyr-triazene-resin LSH-1216 (213 mg, 213 mL, 170 μmol, 1.00 equiv) was swollen in 4 mL of dichloromethane. Then 2,2,2-trifluoroacetic acid (194 mg, 130 μL, 1.70 mmol, 10.0 equiv) and azido(trimethyl)silane (206 mg, 237 μL, 1.70 mmol, 10.0 equiv) were added and the vial was closed. The mixture was shaken for 12 hours at 25 °C. The resin was filtered off and washed with DCM. The combined filtrates were washed with a saturated K2CO3-solution and the solvent was removed under reduced pressure. The crude product was coated on Celite® and purified via flash chromatography (cHex/EtOAc 10:1 --> 4:1) to yield 4-(3-azido-5-methyl-1H-pyrazol-1-yl)benzonitrile (13.9 mg, 62.0 μmol, 58% yield) as a brown solid.