Paper
Organic & Biomolecular Chemistry
and the aqueous layer extracted with dichloromethane (3 ×
10 mL). The combined organic layers were dried over anhy-
drous sodium sulfate and concentrated under reduced
pressure to yield chlorquinaldol analogue 32 (12 mg, 90%).
– 1H NMR (500 MHz): 7.76 (1 H, s), 7.92 (1 H, d, J = 9 Hz), 8.74
(1 H, d, J = 9 Hz) ppm. – 13C NMR (125 MHz): 104.5, 109.89,
117.2, 118.4, 121.0, 125.8, 130.6, 136.1, 137.5, 147.8 (m) ppm.
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–
19F NMR (282 MHz): −82.7, −116.6 ppm. – IR: 960, 1121,
1163, 1331, 1460, 2925, 2963, 3033, 3442 cm−1. – MS (ESI):
331.9, HRMS: 331.9659, calcd: 331.9663 [M + H+].
Acknowledgements
Financial support by the Welch Foundation (AX-1788),
the National Institute of General Medical Sciences
(SC3GM105579), the Max and Minnie Tomerlin Voelcker Fund,
NIH MBRS-RISE (GM060655), and the University of Texas at
San Antonio is gratefully acknowledged. Mass spectroscopic
analysis was supported by a grant from the National Institute
on Minority Health and Health Disparities (G12MD007591).
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