2013
H. G. Bonacorso et al.
Letter
Synlett
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the reaction mixture was stirred at reflux for 2 h and cooled to
r.t. Distilled H2O (15 mL) was then added under magnetic stir-
ring and extracted with CHCl3 (2 × 15 mL). The organic layer
was washed with distilled H2O (2 × 20 mL) and brine (1 × 20
mL), dried over Na2SO4, and the solvent was evaporated under
reduced pressure. Products 8a–c were purified by silica gel
column chromatography, using a mixture of hexane–EtOAc
(95:5 v/v) as eluent.
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1
Yellow solid; yield 65%; mp 135–137 °C. H NMR (400.13 MHz,
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CDCl3): δ = 8.28 (d, J = 9.0 Hz, 2 H), 8.10 (d, J = 8.8 Hz, 2 H), 7.90
(d, 2J = 4.4 Hz, 1 H), 7.69 (d, J = 7.8 Hz, 2 H), 7.48 (t, J = 8.3 Hz, 2
H), 7.34 (t, J = 7.3 Hz, 1 H). 19F NMR (376.3 MHz, CDCl3): δ = –169.9
(d, J = 4.2 Hz). 13C NMR (100.61 MHz, CDCl3): δ = 150.6 (d,
J = 254 Hz), 147.2, 139.6, 137.0 (d, J = 3.8 Hz), 136.6 (d, J = 6.1
Hz), 129.6, 127.2, 126.5 (d, 4J = 4.4 Hz), 124.0, 118.7, 114.7 (d,
2J = 30 Hz). Anal. Calcd for C15H10FN3O2 (283.07): C, 63.60; H,
3.56; N, 14.83. Found: C, 63.60; H, 3.29; N, 14.83.
3
2
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(17) General Procedure with Selectfluor (4b, 8)
Selectfluor (1.1 mmol) was added to a pyrazole solution (10–12,
15–18, 1 mmol) in anhydrous MeCN (5 mL). After the addition,
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