Triethylamine → 3-(2,2-Dimethyl-propyl)-5-(4-fluoro-phenylethyl)-3H-imidazo[4,5-b]pyridin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

Add triethylamine (27.10 g, 267.80 mmol) to a mixture of 5-bromo-3-(2,2-dimethyl-propyl)-3H-imidazo[4,5-b]pyridin-2-yl-ammonium bromide (25.00 g, 68.67 mmol) in ethanol (25 mL) and toluene (75 mL). Heat to 70-75° C. and then add Pd(OAc)2 (0.15 g, 0.69 mmol), triphenylphosphine (0.72 g, 2.75 mmol), and copper (I) iodide (0.13 g, 0.69 mmol). Add ⅔ of a solution of 4-fluorophenylacetylene (12.37 g, 103.00 mmol) in toluene (50 mL, 2.0 vol.) over 15 minutes. Add the remaining 4-fluoroacetylene solution after 1 h. After 3 h, add additional 4-fluorophenylacetylene (1.5 g, 12.86 mmol). After an additional hour, remove EtOH by distillation. Cool the reaction mixture to <40° C. and add water (25 mL). Cool to room temperature. Filter suspension and wash with water (25 mL) and 2×25 mL toluene. Dry under reduced pressure at 45-50° C. to provide 19.3 g (87%) of the desired compound.

Provenance & Evidence