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163
(f) T. Umemoto, S. Ishihara, M. Harada, Daikin, JP 97207900, 1999 (Chem. Abstr.
130:209495).
mixture was heated for 18 h at 50 8C. The reacting mixture was
then filtered and the solid was washed with Et2O. After removing
solvent in vacuo, the filtrate was dissolved in CH2Cl2 and washed
with aqueous NaHCO3 (6%). The organic phase was dried over
Na2SO4 and after removing solvent in vacuo, the crude was purified
by flash chromatography (CH2Cl2/MeOH: 95/5 + 0.5% Et3N).
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(b) S. Large, N. Roques, B.R. Langlois, J. Org. Chem. 65 (2000) 8848–8856;
(c) B. Quiclet-Sire, R.N. Saisic, S.Z. Zard, Tetrahedron Lett. 37 (1996) 9057–9058;
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2180–2182;
Brown solid. Mp = 50–51 8C. 1H NMR (300 MHz, CDCl3):
(bs, 1H), 7.65(m, 1H), 7.36–7.25(massif,2H), 7.14(m, 1H), 3.12–3.10
d = 9.69
(b) L.Z. Gandel’sman, V.N. Boiko, Ukr. Khim. Zh. (Russ. Ed.) 43 (1977) 1224–1225
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(1979) 1245–1253 (Chem. Abstr. 91, 157378);
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6677–6678;
(massif, 4H), 2.27(bs large, 2H). 13C NMR (75 MHz, CDCl3):
d = 138.2,
128.9 (q, 1JC–F = 312 Hz), 127.6, 125.0, 124.6 (q, 4JC–F = 1.1 Hz), 120.5,
120.3, 114.3 (q, 3JC–F = 2.4 Hz), 111.9, 42.7, 29.1. 19F NMR (282 MHz,
CDCl3):
d
= À43.39 (s). Anal. Calcd forC11H11F3N2S: C, 50.76; H, 4.26;
N, 10.76. Found: C, 51.11; H, 4.49; N, 11.04.
(g) C. Wakselman, M. Tordeux, J. Chem. Soc., Chem. Commun. (1984) 793–794;
(h) C. Wakselman, M. Tordeux, J. Org. Chem. 50 (1985) 4047–4051;
(i) C. Wakselman, M. Tordeux, J.L. Clavel, B. Langlois, J. Chem. Soc., Chem.
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4.10. 3-{2-[(Trifluoromethyl)thio]-indol-3-yl}propanoic acid (3h)
To a solution of 1a (1 mmol) in dichloromethane (2 mL) was
added (3-propio)indolic acid (1 mmol) then TsOH (2.5 mmol). The
reaction mixture was heated for 18 h at 50 8C. The reacting mixture
was washed with H2O. The organic phase was dried over Na2SO4 and
after removing solvent in vacuo, the product 3h is directly obtained.
Beige solid. Mp = 103–104 8C. 1H NMR (300 MHz, CDCl3):
`
(l) B. Langlois, N. Roidot, D. Montegre, J. Fluorine Chem. 68 (1994) 63–66;
(m) B. Langlois, T. Billard, N. Roques, J. Org. Chem. 64 (1999) 3813–3820.
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(b) L.M. Yagupolskii, N.V. Kondratenko, G.N. Timofeeva, Zh. Org. Khim. 20 (1984)
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(b) J.F. Harris, J. Am. Chem. Soc. 84 (1962) 3148–3153;
(c) J.F. Harris, J. Org. Chem. 31 (1966) 931–935;
d
= 8.34 (bs, 2H,), 7.66 (m, 1H), 7.40–7.29 (massif, 2H), 7.18 (m,
1H), 3.28 (t, 3J = 8.0 Hz, 2H), 2.74 (t, 3J = 8.0 Hz, 2H). 13C NMR
1
(75 MHz, CDCl3):
125.7 (q, JC–F = 1.1 Hz), 125.3, 120.8, 120.2, 113.9 (q, JC–
F = 2.4 Hz), 111.9, 35.1, 20.5. 19F NMR (282 MHz, CDCl3):
d
= 179.6, 138.0, 128.9 (q, JC–F = 311 Hz), 127.2,
4
3
(d) W. Sheppard, S. Andreades, J.F. Harris, J. Org. Chem. 29 (1964) 898–900;
(e) J. Ippen, B. Baasner, A. Marhold, E. Kysela, S. Dutzmann, P. Reinecke, Bayer
A.G., DE 3836161, 1990 (Chem. Abstr. 113:167366).
d
= À43.22 (s). Anal. Calcd for C12H10F3NO2S: C, 49.82; H, 3.48.
Found: C, 50.05; H, 3.76.
(f) W.A. Sheppard, J. Org. Chem. 29 (1964) 895–898;
(g) K. Sivasankaran, K.S. Rao, K.R. Ratnam, M.S. Mithyantha, K.S. Bhat, Rallis India,
IN 178903, 1997 (Chem. Abstr. 140:375162).;
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