Triethylamine → 2-benzyl 5-methyl 6-amino-1,3-dihydro-2H-isoindole-2,5-dicarboxylate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence