Benzoic acid, 2-amino-5-bromo-3-[2-(trimethylsilyl)ethynyl]-, methyl ester synthesis

Yield:875305-09-2 100%

Reaction Conditions:

with copper (I) iodide;triethylamine;[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) at 20; for 1.5 h;

Steps:

S9

580 mg of 2-amino-5-bromo-3-iodo-benzoic acid methyl ester were dissolved in 6 ml triethylamine. 65 mg of Pd(PPh₃)Cl₂ (0.09 mmol), 18 mg of CuI (0.09 mmol) and 0.285 ml of ethinyltrimethylsilane (2.05 mmol) were added and the mixture was stirred at rt under argon for 1.5 h. The reaction mixture was then diluted with DCM and extracted twice with water followed by brine. The organic phase was finally dried over magnesium sulfate, filtered and concentrated in vacuo, leading to 574 mg of 2-amino-5-bromo-3-trimethylsilanylethynyl-benzoic acid methyl ester as a brown powder (100%). MS (EI) 325 (M)⁺.

References:

US2006/30613,2006,A1 Location in patent:Page/Page column 22