Reaktion #603763
ord-f52efc7b75454131a8a8749944cca95e
Reaktionsgleichung
Edukte
Reagenzien
Lösungsmittel
Reaktionsbedingungen
Aufarbeitung
- 1Sonstigeresulting in a homogeneous yellow solution
- 2SonstigeThe cooled reaction mixture
- 3Extraktionextracted with diethyl ether (4×100 mL)
- 4workup.ADDITIONHexanes (100 mL) was added to the combined organic layers
- 5Waschenthe turbid solution was washed with water (200 mL)
- 6TrocknenThe organic layer was dried (magnesium sulfate), gravity
- 7Filtrationfiltered
- 8Einengenconcentrated by rotary evaporation
- 9SonstigeThe residue was purified by silica gel column chromatography (25% ethyl acetate in hexanes)
Vorschrift
Trimethyl((tributylstannyl)ethynyl)silane (510 mg, 1.3 mmol, 1.1 equiv) was added to a stirred mixture of methyl 4-amino-3-chloro-5-fluoro-6-(4-iodophenyl)picolinate (490 mg, 1.2 mmol, 1.0 equiv) and tetrakis(triphenylphosphine)palladium(0) (140 mg, 0.12 mmol, 0.10 equiv) in N,N-dimethylformamide (2.4 mL) at 23° C. The reaction mixture was heated to 90° C., resulting in a homogeneous yellow solution, and stirred for 20 h. The cooled reaction mixture was diluted with water (200 mL) and extracted with diethyl ether (4×100 mL). Hexanes (100 mL) was added to the combined organic layers and the turbid solution was washed with water (200 mL). The organic layer was dried (magnesium sulfate), gravity filtered, and concentrated by rotary evaporation. The residue was purified by silica gel column chromatography (25% ethyl acetate in hexanes) to afford the title compound as a tan powder (330 mg, 73%): mp 83-86° C.; IR (thin film) 3487 (m), 3375 (s), 2958 (s), 2159 (m), 1739 (s), 1618 (s) cm−1; 1H NMR (300 MHz, CDCl3) δ 7.89 (m, 2H), 7.55 (m, 2H), 4.89 (br s, 2H), 3.99 (s, 3H), 0.26 (s, 9H); ESIMS m/z 377 ([M+H]+).