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step 2—To a solution of 370 (90.0 mg, 0.221 mmol) in pyridine (3 mL) cooled to 0° C. was added 2,2,2 trifluoroethane sulfonyl chloride (40 μL, 0.364 mmol). After 20 min the reaction mixture was warmed to RT and stirred overnight. The reaction mixture was quenched with 30 mL of 1N HCl and thrice extracted with EtOAc (20 mL). The combined extracts were washed with sat'd. aq. CuSO4 (3×30 mL) and brine, dried (Na2SO4), filtered, and concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25 to 35% EtOAc) to afford 88.1 mg (72%) of 2,2,2-trifluoro-ethanesulfonic acid (6-{(E)-2-[3-tert-butyl-5-(5-fluoro-2-methoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-pyridin-3-yl)-amide (372).

1. customThe reaction mixture was quenched with 30 mL of 1N HCl and thrice
2. extractionextracted with EtOAc (20 mL)
3. washThe combined extracts were washed with sat'd
4. dry with materialaq. CuSO4 (3×30 mL) and brine, dried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated
7. customThe crude product was purified by SiO2 chromatography
8. washeluting with an EtOAc/hexane gradient (25 to 35% EtOAc)