反应详情

温度

70 °C

Palladium(II) acetate (46.1 mg, 0.0685 mmol), DPPF (38 mg, 0.0685 mmol), K2CO3 (284 mg, 2.06 mmol) and Et3N (95 uL, 0.685 mmol) were added to a solution of benzyl 5-amino-6-iodo-1,3-dihydro-2H-isoindole-2-carboxylate (270 mg, 0.685 mmol) in MeCN (5 mL) and MeOH (2.5 mL). The reaction mixture was purged with N2, the flask was capped and a CO balloon was attached to it. After bubbling CO gas into the solution through a needle attached to the balloon for 5 min, the mixture was heated under a CO balloon at 70° C. for 4 h. The mixture was diluted with EtOAc (50 mL), filtered through Celite, then washed with water (3×10 mL), brine (1×), dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The residue was purified by flash chromatography on silica gel to provide 2-benzyl 5-methyl 6-amino-1,3-dihydro-2H-isoindole-2,5-dicarboxylate LCMS calc.=327.1; found=326.8 (M+H)+. 1H NMR (500 MHz, CDCl3): δ 7.80-7.75 (2 s, 1H); 7.45-7.35 (m, 5H); 6.61-6.55 (2 s, 1H); 5.79 (br s, 2H); 5.25 (s, 2H); 4.68 (t, J=13.5 Hz, 4H); 3.91-3.90 (2 s, 3H).

1. customThe reaction mixture was purged with N2
2. customthe flask was capped
3. customAfter bubbling CO gas into the solution through a needle
4. additionThe mixture was diluted with EtOAc (50 mL)
5. filtrationfiltered through Celite
6. washwashed with water (3×10 mL), brine (1×)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. customthe solvent was evaporated in vacuo
10. customThe residue was purified by flash chromatography on silica gel