Potassium Phosphate, Tribasic → (3aR,6aR)-4'-(5-Methyl-hexahydro-pyrrolo[3,4-b]pyrrol-1-yl)-biphenyl-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

The product of Example 7C (30.0 mg, 0.11 mmole), 4-cyanophenylboronic acid (18.8 mg, 0.13 mmole), palladium(II) acetate (1.2 mg, 0.005 mmole), 2-(dicyclohexylphosphino)biphenyl (3.8 mg, 0.01 mmole) and potassium phosphate (K3PO4) (75 mg, 0.35 mmole) were dissolved in 1 ml of toluene, 0.5 ml of isopropanol and 0.5 ml of water. The mixture was stirred at 60° C. under N2 for 5 hours. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (5×). The combined organics were dried over sodium sulfate, filtered and concentrated and purified by chromatography (eluting with a mixture of 5% methanol in dichloromethane) to provide the title compound (23.1 mg, 71.3%). 1H NMR (300 MHz, CDCl3) δ ppm 7.60-7.68 (m, 4H) 7.47-7.53 (m, 2H) 6.61-6.68 (m, 2H) 4.14-4.22 (m, 1H) 3.51-3.60 (m, 1H) 3.28-3.35 (m, 1H) 2.93-3.01 (m, 1H) 2.71-2.75 (m, 1H) 2.48-2.61 (m, 3H) 2.32 (s, 3H) 2.14-2.25 (m, 1H) 1.96 (d, J=7.12 Hz, 1H). MS; (M+H)+=281/283.

Provenance & Evidence