反应详情

To a solution of 5-bromo-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ethyl ester (Preparation 26, 0.160 g, 0.590 mmol) in DMF (anhydrous, 5 mL) was added zinc (II) cyanide (0.041 g, 0.35 mmol) then tetrakis-triphenylphosphine palladium (0). The reaction mixture was degassed by bubbling argon through it for 10 min. The reaction mixture was heated to reflux temperature for 4.5 h then allowed to cool to rt. Water (30 mL) was added and the mixture extracted with ethyl acetate (2×50 mL). The combined organics were washed with brine (30 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate then adsorbed onto silica gel. Purification via flash column chromatography (SiO2, ethyl acetate:isohexane, 1:3, v/v) gave the title compound as a white solid. δH (CDCl3): 1.45 (3H, t), 4.49 (2H, quartet), 7.31 (1H, s), 8.09 (1H, s), 8.97 (1H, s), 9.60 (1H, br s); m/z (ES+)=216 [M+H]+; RT=3.03 min.

1. customThe reaction mixture was degassed
2. customby bubbling argon through it for 10 min
3. temperatureThe reaction mixture was heated
4. temperatureto reflux temperature for 4.5 h
5. additionWater (30 mL) was added
6. extractionthe mixture extracted with ethyl acetate (2×50 mL)
7. washThe combined organics were washed with brine (30 mL)
8. dry with materialdried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. dissolutionThe residue was dissolved in ethyl acetate
12. customPurification via flash column chromatography (SiO2, ethyl acetate