Trimethylsilylacetylene → HCID 178463856, compound

Participants

Reaction Conditions

Reaction Steps

The synthesis was performed following a procedure of Stara, Irena G.; Stary, Ivo; Kollarovic, Adrian; Teply, Filip; Saman, David; Fiedler, Pavel. Coupling reactions of halobenzenes with alkynes. The synthesis of phenylacetylenes and symmetrical or unsymmetrical 1,2-diphenylacetylenes. Collect. Czech. Chem. Commun. (1999), 64(4), 649-672. A solution of 0.405 g (1.00 mmol) of [5-(3-bromo-phenyl)-4-methyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone in 5 ml piperidine was degassed (argon) and treated with 58 mg (0.05 mmol) Pd(PPh3)4 and 10 mg (0.05 mmol) CuI. The reaction mixture was stirred at 50° C. for 10 min and then slowly (60 min) treated with 0.17 ml (1.20 mmol) of ethynyltrimethylsilane in 5 ml piperidine. After 30 min the bath was slowly (30 min) heated to 80° C. The reaction mixture was stirred at this temperature for 2.5 h and then partitioned between chilled water sat. KHCO3/EtOAc (3×). The organic phases were washed with aqueous 10% NaCl, dried (Na2SO4) and evaporated. Purification by flash-chromatography on silica gel (CH2Cl2/MeOH 98:2 to 92:8) yielded 0.27 g (64%) of the title compound as yellow viscous oil. MS: 423.3 (MH+).

Provenance & Evidence