Triethylamine → HCID 58063622, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-bromo-3-fluorophenyl)pyridine (55 mg, 0.218 mmol), CuI (5.8 mg, 0.031 mmol), PdCl2(PPh3)2 (23 mg, 0.033 mmol) were placed in a μwave tube under an atmosphere of N2. TMS acetylene (46 μL, 0.327 mmol), Et3N (121 μL, 0.873 mmol) and THF (1.1 mL) were added and the mixture was heated to 100° C. for 20 min and then cooled to ambient temperature. The mixture was filtered through a silica gel pack and washed with EtOAc. Combined eluents were evaporated under reduced pressure to give crude TMS acetylenic product as a solid. The crude material from step 1 was dissolved in MeOH (in some cases 20% EtOAc was added to increase solubility) and 3 eq of K2CO3 added and the mixture stirred for 30 min. To the mixture was added water and extracted with EtOAc. The combined organic layers were dried, filtered and evaporated. The residue was purified by column chromatography on silica to afford the title compound 29 mg (0.146 mmol).

Provenance & Evidence