Trimethyl((tributylstannyl)ethynyl)silane → 8-Chloro-4-ethynyl-2-(3-fluoro-4-hydroxyphenyl)quinolin-6-ol

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Reaction Steps

This compound was prepared from 45a following a combination of method J using (trimethylsilylethynyl)tributyltin and method L. Yellow solid; Yield: 73%; mp 210° C. (dec.); 1H-NMR (400 MHz, DMSO-d6) δ 5.06 (s, 1H), 7.09 (dd, J=8.9, 8.8 Hz, 1H), 7.45 (d, J=2.6 Hz, 1H), 7.56 (d, J=2.6 Hz, 1H), 8.00 (dd, J=8.5, 1.7 Hz, 1H), 8.12 (dd, J=12.9, 2.2 Hz, 1H), 8.26 (s, 1H), 10.34 (s, 1H), 10.60 (s, 1H); 19F-NMR (400 MHz, DMSO-d6) δ −136.30 (dd, J=13.2, 9.3 Hz); MS (ESI) m/z 312/314 ([M−H]−), 314/316 ([M+H]+); Anal. Calcd for C17H9ClFNO2: C, 65.09; H, 2.89; N, 4.46. Found: C, 64.86; H, 3.14; N, 4.05.

Provenance & Evidence