Diisopropylethylamine → HCID 86669619, compound

Participants

Reaction Steps

To 900 mg (2.73 mmol) N-(1-(4-iodophenyl)propan-2-yl)cyclopropanecarboxamide (I52.3) and 0.56 mL (3.01 mmol) (tert-butyldimethylsilyl)acetylene in 5 mL THF at 0° C. are added 0.77 mL (5.48 mmol) DIPEA, 96.1 mg (0.14 mmol) bis(triphenyl-phosphine)dichloropalladium and 53.1 mg (0.28 mmol) CuI, and the reaction mixture is stirred at r.t. over night. The mixture is diluted with water and extracted with DCM (2×). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, DCM/MeOH 98/2) to yield the silylated compound. To this substance in DCM are added 949 mg (3.01 mmol) TBAF*3H2O and the mixture is stirred at r.t. for 3 h. The mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, DCM/MeOH 98/2).

Provenance & Evidence