N,N-diphenyl-4-((trimethylsilyl)ethynyl)aniline synthesis

6synthesis methods

Product Name:N,N-diphenyl-4-((trimethylsilyl)ethynyl)aniline
CAS Number:205877-25-4
Molecular formula:C23H23NSi
Molecular Weight:341.52

36809-26-4 Synthesis

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N,N-diphenyl-4-((trimethylsilyl)ethynyl)aniline

205877-25-4
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Yield:205877-25-4 97.3%

Reaction Conditions:

Stage #1: 4-N,N-diphenylamino-1-bromobenzenewith (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;copper(l) iodide;triphenylphosphine for 0.25 h;Microwave irradiation;Inert atmosphere;
Stage #2: trimethylsilylacetylenewith triethylamine at 80;Microwave irradiation;Inert atmosphere;

Steps:

3.4. N,N-Diphenyl-4-((trimethylsilyl)ethynyl)aniline

N,N-Diphenyl-4-((trimethylsilyl)ethynyl)aniline was prepared in the same manner as N,N-dimethyl-4-((trimethylsilyl)ethynyl)aniline [68] rather than by the previously described method [72]. 4-Bromophenylamine (1.002 g, 3.09 mmol, 5.0 eq), Pd(dppf)Cl2 (136 mg, 185 μmol, 6 mol%), CuI (58.8 mg, 309 μmol, 0.5 eq) and PPh3 (81.0 mg, 309 μmol, 0.5 eq) were loaded in a 10 mL microwave vial, degassed and purged with N2 three times. After 15 min of N2 purging, 2 mL of Et3N were added to the mixture and set under stirring. Finally, trimethylsilylethyne (910 mg, 9.27 μmol, 15 eq) was added to the reaction mixture and was set at 80 °C overnight. After cooling down to room temperature, the mixture was poured in water (10 mL) and extracted with AcOEt (3 x 10 mL), the organic layers were washed further with brine (30 mL) and back-extracted. The organic layers were collected together, dried over MgSO4, and dried under reduced pressure. The crude mixture was purified by column chromatography (Biotage Sf?r silica HC D, petroleum ether/CH2Cl2, CH2Cl2 increasing gradient up to 10%). The product was isolated as a brown solid (1.027 g, 3.007 mmol, 97.30%). 1H NMR (500 MHz, CDCl3): δ/ppm 7.33 (d, J = 8.7 Hz, 2H), 7.27 (m, 4H), 7.08 (m, 4H), 7.06 (m, 2H), 6.95 (d, J = 8.7 Hz, 2H), 0.26 (s, 9H) as reported in the literature [73].

References:

Becker, Mariia;Constable, Edwin C.;Housecroft, Catherine E.;Risi, Guglielmo [Molecules,2020,vol. 25,# 7]

38257-52-2 Synthesis