Sodium t-butoxide → HCID 67285151, compound

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Prepared according to procedure Y using 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (29.6 mg, 0.109 mmol), 6-morpholin-4-yl-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide (35 mg, 0.109 mmol), sodium tert-butoxide (20.9 mg, 0.217 mmol) and XPhos precatalyst (8.02 mg, 10.86 μmol). Purification by reverse phase HPLC gave 1-(7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)-6-(4-morpholinyl)-1,2,2′,3′,5′,6′-hexahydrospiro[indole-3,4′-thiopyran]1′,1′-dioxide. 1H NMR (400 MHz, chloroform-d) δ ppm 8.74 (1H, dt, J=4.9, 1.4 Hz), 7.82-7.96 (3H, m), 7.75 (1H, dd, J=9.2, 6.1 Hz), 7.39-7.44 (1H, m), 7.24-7.29 (1H, m), 7.19 (1H, d, J=8.2 Hz), 6.35 (1H, dd, J=8.2, 2.2 Hz), 5.61 (1H, d, J=2.2 Hz), 3.94-3.99 (1H, m), 3.87-3.92 (1H, m), 3.68-3.78 (4H, m), 3.07-3.26 (4H, m), 2.91-3.03 (4H, m), 2.61-2.76 (2H, m), 2.29-2.49 (5H, m). Mass Spectrum (ESI) m/e=559.0 (M+1)

Provenance & Evidence