Acetic Acid → 2-[3-(1-Piperidinylmethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Conditions

Reaction Steps

3-(Dibromomethyl)-2-(phthalimidyl)pyridine (185 mg, 0.47 mmol) was dissolved in CH2Cl2 (2 mL) and treated with piperidine (0.460 mL, 4.66 mmol), and glacial AcOH (0.160 mL, 2.80 mmol) in a dropwise fashion. The resulting yellow solution was stirred at 23° C. for 2 h, then treated with solid NaBH(OAc)3 (393 mg, 1.86 mmol) in one portion, and stirring was continued for 14 h. After stirring 14 h at 23° C., the mixture was treated with 2M K2CO3 (6 mL), and stirred for 1 h. After 1 h, the mixture was diluted with EtOAc (50 mL) and washed with H2O (1×50 mL), and saturated NaCl (1×50 mL). The organic phase was then dried (MgSO4) and concentrated in vacuo to provide the title compound as a yellow residue. The crude material was used in subsequent transformations without further purification. MS m/z: 323 (M+H).

Provenance & Evidence