4-(Trifluoromethyl)phenylboronic acid → HCID 58056548, compound

Participants

Reaction Steps

In a micro wave test tube, 3-[1-(5-bromo pyridine-3-sulfonyl)-5-chloro-1H-indol-3-yl]propionic acid methyl ester (11, 40 mg, 0.00009 mol), 4-(trifluoromethyl)-phenylboronic acid (12, 52 mg, 0.00027 mol), and tetrakis(triphenylphosphine)palladium(0) (4 mg, 0.000003 mol) were combined in 4 mL of 1,4-dioxane. The vessel was purged with argon for 2-3 minutes, then 0.1 mL of 1N K2CO3 was added. The vessel was microwaved at 108° C. for 40 minutes. TLC (20% ethyl acetate,/hexane) indicated a new spot and total disappearance of starting material. The crude mixture was transferred to a separatory funnel and extracted with 3×40 mL of ethyl acetate and washed with water, brine, and dried over MgSO4. The solution was filtered and the filtrate roto evaporated to near dryness. Silica and 5 mL of ethyl acetate were added and the solvent removed. Chromatography was run using a gradient solvent condition of 0 to 20% ethyl acetate/hexane over 18 minutes, then 20 to 30% over 10 minutes to isolate the desired compound. 1H NMR consistent with structure.

Provenance & Evidence