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0 °C

To a stirred solution of tert-butyl 4-(5-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridin-2-yl)piperazine-1-carboxylate (724 mg, 1.67 mmol) in CH2Cl2 (8 mL) at 0° C. was added trifluoroacetic acid (4 mL). The reaction was brought to room temperature and stirred for 30 minutes. Volatiles were removed in vacuo. The residue was then dissolved in CH2Cl2 (20 mL) and washed with aqueous sodium hydroxide solution (2M, 2×20 mL). The layers were then separated and the aqueous phase extracted with CH2Cl2 (3×10 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo. The residue was dissolved in CH2Cl2 (50 mL), and cooled to 0° C. and treated sequentially with triethylamine (0.25 mL, 1.75 mmol) and methanesulfonyl chloride (0.14 mL, 13.5 mmol). The reaction was brought to RT and stirred for 1 hour. The reaction was then quenched with water (50 mL). The layers were separated and the aqueous phase extracted with CH2Cl2 (3×20 mL). The combined organic extracts were then dried, (MgSO4), filtered and concentrated in vacuo to give 1-(methylsulfonyl)-4-(5-{[5-(trifluoromethyl)pyridin-2-yl]ethynyl}pyridin-2-yl)piperazine as an orange solid (445 mg, 1.08 mmol, 65%).

1. customwas brought to room temperature
2. customVolatiles were removed in vacuo
3. dissolutionThe residue was then dissolved in CH2Cl2 (20 mL)
4. washwashed with aqueous sodium hydroxide solution (2M, 2×20 mL)
5. customThe layers were then separated
6. extractionthe aqueous phase extracted with CH2Cl2 (3×10 mL)
7. dry with materialThe combined organic extracts were then dried, (MgSO4),
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
11. customwas brought to RT
12. stirringstirred for 1 hour
13. customThe reaction was then quenched with water (50 mL)
14. customThe layers were separated
15. extractionthe aqueous phase extracted with CH2Cl2 (3×20 mL)
16. dry with materialThe combined organic extracts were then dried, (MgSO4),
17. filtrationfiltered
18. concentrationconcentrated in vacuo