Potassium Fluoride → HCID 58497205, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 133 compound (34 mg, 0.067 mmol), thiophene tin reagent (22.34 μl, 0.0704 mmol) and Pd(PPh3)4 (77.42 mg, 0.067 mmol) in dioxane (1 ml) was vacuumed and purged to N2 for 3 times, then reaction mixture was heated at 110° C. for 4 hrs. The reaction mixture was cooled to rt, added KF (sat, 1 ml), stirred at rt for one hour, filtered, washed with EtOAc, and separated to two layers. The organic layer was washed with brine, dried, filtered, concentrated, and separated by prep TLC (CH2Cl2:Hex:EtOAc=3:3:1) to afford 5-[(4-chlorophenyl)sulfanyl]-1-methyl-4-[4-(methylsulfonyl)phenyl]-2-(thiophen-2-yl)-1H-imidazole (25 mg). 1H NMR (500 MHz), [CDCl3]: 8.38 (m, 2H), 7.95 (m, 2H), 7.50 (m, 2H), 7.40 (m, 2H), 7.15 (m, 1H), 7.10 (m, 2H), 3.82 (s, 3H), 3.05 (s, 3H). LCMS: [M+1]+=461.0. Human FAAH lysate assay: IC50=16.5 nM.

Provenance & Evidence