반응 #730657

반응 방정식

2-bromo-4-[(4-methoxy-3-methylphenyl)(oxo)acetyl]benzonitrile

3-(tributylstannyl)pyridine

→

title compound

수율 91.0%

4-[(4-Methoxy-3-methylphenyl)(oxo)acetyl]-2-pyridin-3-ylbenzonitrile

수율 91.0%

용매

1,2-diethoxyethane

반응 조건

후처리

1. 1
   여과filtered
2. 2
   기타to remove the catalyst
3. 3
   기타The filtrate is evaporated to dryness
4. 4
   기타The resultant residue is purified by flash chromatography (SiO2, 2/1 hexanes/EtOAc as eluent) and crystallization from ethyl ether/hexanes

실험 절차

A mixture of 2-bromo-4-[(4-methoxy-3-methylphenyl)(oxo)acetyl]benzonitrile (200 mg, 0.56 mmol) and 3-(tributylstannyl)pyridine (268 mg, 0.73 mmol) in 1,2-diethoxyethane is treated with dichlorobis(tri-o-tolylphosphine)palladium(II) (39.6 mg, 0.05 mmol), heated at 145° C., stirred for 30 min. and filtered to remove the catalyst. The filtrate is evaporated to dryness. The resultant residue is purified by flash chromatography (SiO2, 2/1 hexanes/EtOAc as eluent) and crystallization from ethyl ether/hexanes to afford the title compound as a yellow solid, 181 mg (91% yield), identified by HNMR and mass spectral analyses. MS m/e 357 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 2.21 (s, 3H), 3.93 (s, 3H), 7.18 (d, J=8.69 Hz, 1H), 7.61 (m, 1H), 7.82 (d, J=8.54, 1H), 7.84 (dd, J=8.54, 1.99 Hz 1 H), 8.07 (dd, J=7.76, 1.67 Hz, 1H), 8.12 (m, J=1.38 Hz, 2H), 8.25 (d, J=8.08 Hz, 1H), 8.74 (m, 1H), 8.85 (d, 1.68 Hz, 1H).

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