Reaktion #603761

Reaktionsgleichung

methyl 4-amino-3-chloro-6-(4-iodophenyl)-5-methylpicolinate

trimethyl((tributylstannyl)ethynyl)silane

→

title compound

Ausbeute 21.1%

methyl 4-amino-3-chloro-5-methyl-6-(4-((trimethylsilyl)ethynyl)phenyl)picolinate

Ausbeute 21.1%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Extraktiondiluted water, and extracted with ethyl acetate (2×)
3. 3
   TrocknenThe organic layers were dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   SonstigePurification by flash chromatography (0-100% ethyl acetate/hexanes)

Vorschrift

A mixture of methyl 4-amino-3-chloro-6-(4-iodophenyl)-5-methylpicolinate (264 mg, 0.66 mmol), trimethyl((tributylstannyl)ethynyl)silane (280 mg, 0.72 mmol), tetrakis(triphenylphosphine)palladium(0) (75 mg, 0.065 mmol) in anhydrous DMF (1.3 mL) was heated at 90° C. for 16 h. The reaction was cooled, diluted water, and extracted with ethyl acetate (2×). The organic layers were dried over anhydrous magnesium sulfate, filtered, and adsorbed onto silica gel. Purification by flash chromatography (0-100% ethyl acetate/hexanes) afforded the title compound as a brown solid (52 mg, 21%): mp 158-164° C.; 1H NMR (400 MHz, CDCl3) δ 7.52 (d, J=8.5 Hz, 2H), 7.40 (d, J=8.5 Hz, 2H), 4.83 (s, 2H), 3.96 (s, 3H), 2.14 (s, 3H), 0.26 (s, 9H); IR (neat film) 3325, 3227, 2955, 2157, 1729, 1629, 1246 cm−1; ESIMS m/z 372 ([M]+).

Quelle