Potassium Carbonate → 2-(3-{5-[4-(1,3-Dioxo-isoindol-2-yl)-butyl]-pyridin-2-yl}-propyl)-isoindole-1,3-dione

Participants

Reaction Steps

To a stirred solution of 3-3 (9.1 g, 45.4 mmol) in degassed THF (50 mL) at 0° C. was added dropwise a solution of 9-BBN (110 mL of 0.5M in THF, 55 mmol) and the mixture stirred for 18 hours at ambient temperature. K2CO3 (10.8 g, 77.4 mmol) and 3-2 (5.0 g, 17.4 mmol) were added, followed by a premixed and aged (70° C. for 30 min) suspension of Pd(OAc)2 (1.2 g, 5.2 mmol) and DPPF (3.2 g, 5.6 mmol) in degassed DMF (50 mL). The resulting mixture was stirred for 18 hours at 70° C., cooled, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica gel (40-50% EtOAc/hexane) to give 6.2 g of 3-4 as a white solid.

Provenance & Evidence