Hydrochloric Acid → 3-(3-((5-(3-Fluoro-2-(trifluoromethyl)phenyl)furan-2-yl)methylene)-3,4,5,6-tetrahydropyridin-2-yl)pyridine dihydrochloride

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Intermediate 5 (190 mg, 0.67 mmol) (prepared as described in Example 35) was dissolved into a 1:1 mixture of toluene (20 mL) and 1,4-dioxane (10 mL) in a reaction vessel. 3-Fluoro-2-(trifluoromethyl)bromobenzene (326 mg, 1.34 mmol), Pd(PPh3)4 (81 mg, 0.07 mmol), and 2 M Na2CO3(aq) (670 μL, 1.34 mmol) were added and the reaction vessel flushed with N2 and sealed. The reaction mixture was heated to 110° C. with stirring overnight. The reaction was then cooled to room temperature, filtered through Celite®, and the filtrate concentrated under reduced pressure. The recovered material was then treated with water and extracted three times with EtOAc. The EtOAc extracts were washed with brine, combined, dried over Na2SO4, filtered and concentrated under reduced pressure. The recovered material was then eluted through a 20 gram column of silica gel with 98:2:0.2 CH2Cl2:MeOH:NH4OH (1 liter). The material recovered from this column was eluted through a second 20 gram column of silica gel with an 8.5:7:7:0.5:0.05 (685 mL) and with 7:7:7:1:0.1 (440 mL) Hexane:MtBE:CH2Cl2: MeOH:NH4OH step gradient. The recovered material was dissolved into MeOH and treated with 2 eq. of 6 N HCl(aq). This solution was then concentrated under reduced pressure and the recovered material re-crystallized from a mixture of hot ethanol and isopropanol. The crystals were recovered by vacuum filtration and washed with a 20% solution of isopropanol in hexane, and then with ether, then dried under vacuum giving 29 mg (9%) of a golden yellow solid. LC-MS: RT=5.88 min, [M+H]+=401.0.

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