Phenylacetylene → HCID 68866633, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve (6-chloro-3-nitropyridin-2-yl)-(2,2-dimethylpropyl)amine (7.3 g, 30.0 mmol), phenylacetylene (5.0 mL, 45 mmol) and triphenylphosphine (1.5 mmol, 0.39 g) in triethylamine (10 mL/g) in an oven-dried round bottom flask is flushed with nitrogen and evacuated three times. Add Pd(OAc)2 (0.10 g, 0.45 mmol) and the nitrogen flush/evacuation cycle is repeated (3×). Heat at 70-80° C. with stirring under nitrogen for 1-3 h, then cool at RT for 2 h. Concentrate and partition between water (25 mL) and EtOAc (150 mL). Separate the organic layer and wash with water (4×25 mL), saturated aqueous NaCl (25 mL), dry with MgSO4, filter, and concentrate. Purify the crude solid by recrystallization from EtOAc/hexanes to give the title product as a bright orange solid (6.5 g, 21.2 mmol, 71%).

Provenance & Evidence