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B. Niu et al.
Letter
Synlett
Reference and Notes
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(10) General Procedure for the Synthesis of Nitromethyl-Substi-
tuted Oxindole Derivatives
N-Methyl-N-(phenylsulfonyl)methacrylamide (2.0 mmol, 1.0
equiv) was added to a dried sealed tube, followed by the addi-
tion of NaHCO3 (2 mmol, 1.0 equiv), NaNO2 (4.0 mmol, 2 equiv),
K2S2O8 (2.0 equiv), and anhydrous MeCN (2 mL). The reaction
mixture was stirred at 120 °C for 18 h. After the reaction was
completed, the reaction mixture was cooled down to r.t. and
diluted with EtOAc, then the combined organic layers were
dried over Na2SO4, filtered, and concentrated in vacuum. The
residue was purified by flash chromatography (PE–EtOAc, 25:1)
to provide the title compound 3a as a sticky solid in a 88% yield.
The same procedure for producing other compounds 3b–j.
1-Isopropyl-3-methyl-3-(nitromethyl)indolin-2-one (3a)
Sticky solid. IR: 2925, 2854, 2359, 1714, 1611, 1556, 1452,
1357, 1213, 754 cm–1. 1H NMR (400 MHz, CDCl3): δ = 7.33–7.04
(arom. H, 4H), 4.96 (d, J=13.2 Hz, 1H), 4.77 (d, J=13.6 Hz, 1H),
4.68 (m, 1H), 1.56 (d, J=7.2 Hz, 6H), 1.40 (s, 3H) ppm. 13C NMR
(100 Hz, CDCl3): δ = 21.9, 29.4, 31.9, 44.3, 46.8, 79.1, 110.5,
122.6, 129.0, 129.5, 142.4, 177.0. ESI-MS: m/z calcd for
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K.; Pettit, G. R. Tetrahedron Lett. 1995, 36, 2783. (b) Volk, B.;
Barkoczy, J.; Hegedus, E.; Udvari, S.; Gacsalyi, I.; Mezei, T.;
Pallagi, K.; Kompagne, H.; Levay, G.; Egyed, A.; Harsing, L. G.;
Spedding, M.; Simig, G. J. Med. Chem. 2008, 51, 2522.
(c) Christensen, M. K.; Erichsen, K. D.; Trojel-Hansen, C.;
Tjornelund, J.; Nielsen, S. J.; Frydenvang, K.; Johansen, T. N.;
C
13H16N2O3: 249.1239 [M + H]+; found: 249.1249.
© Georg Thieme Verlag Stuttgart · New York — Synlett 2015, 26, 635–638