5-aMino-6-(3-(diMethylaMino)phenyl)-1-naphthonitrile synthesis

Yield:1240642-74-3 106 mg

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾;sodium carbonate in ethanol;water;benzene; for 24 h;Reflux;Inert atmosphere;

Steps:

EXAMPLE S

The mixer containing 2 (95 mg), 3-dimethylaminophenylboronic acid (62 mg, 1.0 eq), Pd(PPh₃)₄ (10 mg, 0.02 eq) and Na₂CO₃ (320 mg, 8.0 eq) in 8 mL of H₂O: EtOH: Benzene (v/v 3:3:10) was refluxed for 24 hrs under argon atmosphere. The reaction mixture was poured into H₂O and extracted with CH₂Cl₂. The crude product after evaporation was purified by flash column using CH₂Cl₂ to yield NO₅₅₀ (106 mg, 99%). ¹HNMR (400 MHz, CDCl₃) δ 8.13 (d, 1H, J=8.8 Hz), 7.89 (dd, 1H, J=7.2, 1.2 Hz), 7.73 (dd, 1H, J=8.4, 1.2 Hz), 7.54 (d, 1H, J=8.4 Hz), 7.50 (dd, 1H, J=8.8, 7.2 Hz), 7.38 (dd, 1H, J=7.6, 7.6 Hz), 7.26 (s, 1H), 6.84-6.77 (m, 3H), 4.48 (s, 2H), 3.008 (s, 6H). ¹³CNMR (400 MHz, CDCl₃) δ 151.7, 140.5, 140.2, 133.4, 133.0, 132.1, 130.5, 127.3, 125.4, 124.5, 123.9. 118.9, 118.0, 115.8, 113.9, 112.4, 111.1, 41.2. HRMS m/z=288.1500 (M+H^|), calculated 288.1495.

References:

US2013/302903,2013,A1 Location in patent:Paragraph 0056; 0058