HCID 67235911, compound → HCID 67235947, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL round bottom flask was charged with 4-(2-amino-5-bromo-phenylethynyl)-piperidine-1-carboxylic acid tert-butyl ester (5.90 g, 15.6 mmol), dichlorobis(benzonitrile)palladium (II) (1.20 g, 3.13 mmol), and dimethylformamide (175 mL) and the resulting mixture heated to 80° C. for 24 h. The resulting mixture was then concentrated in-vacuo and the residue purified via flash silica gel chromatography (Analogix IF-280, SF25-40 g column, gradient 90:10-80:20 Heptane:EtOAc) to yield tert-butyl 4-(5-bromo-1H-indol-2-yl)piperidine-1-carboxylate. 1H NMR (300 MHz, CDCl3) δ 7.66 (s, 1H), 7.16-7.23 (m, 2H), 6.20 (s, 1H), 2.84-3.02 (m, 5H), 1.97-2.04 (m, 2H), 1.61-1.74 (m, 2H), and 1.48 (s, 9H); MS (ES+) 380 (M+1).

Provenance & Evidence