2-Bromothiazole → (3aR,6aR)-5-methyl-1-{4-[4-(1,3-thiazol-2-yl)piperazin-1-yl]phenyl}octahydropyrrolo[3,4-b]pyrrole

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The product of Example 49B (50 mg, 0.175 mmole), 2-bromothiazole (35 mg, 0.21 mmole), tris(dibenzylideneacetone)dipalladium (3.2 mg, 0.0035 mmole), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (4.4 mg, 0.007 mmole) and sodium tert-butoxide (25.2 mg, 1.5 mmole) were dissolved in 1 ml of toluene and heated at 80° C. under N2 for 24 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, concentrated under reduced pressure and was purified by chromatography (eluting with a mixture of 5% methanol in dichloromethane) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.22 (d, J=3.73 Hz, 1H) 6.88-6.96 (m, 2H) 6.59 (d, J=3.73 Hz, 1H) 6.50-6.58 (m, 2H) 4.06-4.22 (m, 1H) 3.60-3.69 (m, 4H) 3.48-3.58 (m, 1H) 3.17-3.27 (m, 1H) 3.11-3.17 (m, 4H) 2.95-3.07 (m, 1H) 2.61-2.71 (m, 4H) 2.41(s, 3H) 2.10-2.22 (m, 1H) 1.93-1.97 (m, 1H); MS (M+H)+=370.

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