{5-[2-Amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester → tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propylcarbamate

Participants

Reaction Conditions

Reaction Steps

A 500 mL round bottom flask was charged with {5-[2-amino-5-(3,4-dimethoxy-phenylcarbamoyl)-phenyl]-pent-4-ynyl}-carbamic acid tert-butyl ester (3.0 g, 6.62 mmol), dichlorobis(benzonitrile)palladium (II) (0.514 g, 1.34 mmol), and dimethylformamide (80 mL) and the resulting mixture heated to 80° C. for 24 h. The resulting mixture was then concentrated in-vacuo and the residue via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 100:0-90:10 CH2Cl2:MeOH) to yield tert-butyl 3-(5-(3,4-dimethoxyphenylcarbamoyl)-1H-indol-2-yl)propylcarbamate. MS (ES+) 454 (M+1); HPLC: Kromasil C18 column (50×2 mm; 3.5μ), gradient 1{tilde over (0)}90% (MeCN+0.16% TFA) in (water+0.2% TFA) over 4 min, tR=3.78 min.

Provenance & Evidence