N-[5-(2-aminophenyl)pent-4-ynyl]-2-(S)-(2,2,2-trifluoroacetylamino)butyramide → (S)-N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide

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Reaction Conditions

Reaction Steps

A 50 mL round bottom flask was charged with N-[5-(2-aminophenyl)pent-4-ynyl]-2-(S)-(2,2,2-trifluoroacetylamino)butyramide (130 mg, 0.37 mmol), dichlorobis(benzonitrile)palladium (II) (38.0 mg, 0.099 mmol), and dimethylformamide (4.1 mL) and the resulting mixture heated to 80° C. for 22 h. The resulting mixture was then concentrated in-vacuo and the resulting residue purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-50:50 Heptane:EtOAc) to yield (S)—N-(3-(1H-indol-2-yl)propyl)-2-(2,2,2-trifluoroacetamido)butanamide. 1H NMR (300 MHz, CDCl3) δ 7.48-7.53 (m, 1H), 7.32 (d, J=7.9 Hz, 1H), 7.04-7.15 (m, 2H), 6.23 (s, 1H), 4.32-4.39 (m, 1H), 3.31-3.38 (m, 2H), 2.71-2.75 (m, 2H), 1.82-1.95 (m, 3H), 1.63-1.77 (m, 1H), and 0.90-0.95 (m, 3H); MS (ES+) 356 (M+1).

Provenance & Evidence