Cesium carbonate → 3-({4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]benzyl}amino)benzonitrile

Participants

Reaction Conditions

Reaction Steps

The product of Example 69 (40 mg, 0.173 mmole), 3-bromobenzonitrile (47 mg, 0.258 mmole), tris(dibenzylideneacetone)dipalladium (16 mg, 0.017 mmole), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (21 mg, 0.034 mmole) and cesium carbonate (85 mg, 0.26 mmole) were dissolved in 1 ml of toluene and heated at 100° C. under N2 for 48 hours. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (3×). The combined organics were dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by chromatography (eluting with a mixture of 2% basic methanol in dichloromethane) to provide the title compound. 1H NMR (CDCl3) δ ppm 9.73 (s, 1H) 7.72 (d, J=8.82 Hz, 2H) 7.30-7.54 (m, 2H) 7.14-7.22 (m, 1H) 6.77-6.88 (m, 1H) 6.56 (t, J=8.65 Hz, 2H) 4.22-4.33 (m, 1H) 4.19 (s, 2H) 3.36-3.64 (m, 2H) 2.90-3.08 (m, 1H) 2.66-2.79 (m, 2H) 2.52-2.63 (m, 2H) 2.32 (s, 3H) 2.09-2.26 (m, 1H) 1.87-2.04 (m, 1H); MS (M+H)+=333.

Provenance & Evidence