A. Krishnaiah, B. Narsaiah / Journal of Fluorine Chemistry 115 (2002) 9–11
11
[8] H. Shimotori, T. Ishii, H. Yamazaki, T. Kuwatsuka, Y. Yanase, Y.
Tanaka, GP 3,713,744 (1987); Chem. Abstr. (1988) 108, 112445d.
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Roberts. Eur. Pat. Appl. 295 (1988) 117; Chem. Abstr. (1990) 112,
35845n.
(2 ml) was added. The reaction mixture was heated at 140 8C
bath temperature for 6 h. Then the mass was allowed to cool
to room temperature and transferred onto crushed ice. The
separated solid was collected on a Buchner funnel, dried and
purified by column chromatography.
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Abstr. (1983) 98, 72087e.
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631.
3.3.1. 3-Amino-4-trifluoromethyl-6-phenyl-N-methyl
pyrazole[3,4-b] pyridine (5a)
Yield 44%, mp 196 8C, IR (KBr): 3460, 3300, 3200,1375,
1275, 1125 cmÀ1. H NMR (CDCl3): d 4.00 (s, 3H, CH3);
1
4.25 (s, 2H, NH2); 7.5 (m, 3H, ArH); 7.65 (s, 1H, H–C(5));
8.10 (m, 2H, ArH) ppm. MS: m/z 292 (Mþ, base peak); 263,
228, 77; analysis: calcd. for C14H11F3N4: C, 57.53; H, 3.79;
N, 19.16%. Found: C, 57.38; H, 3.63; N, 19.05%.
[16] H.-P. Guan, X.-Q. Tang, B.-H. Luo, C.-M. Hu, Synthesis (1997)
1489.
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(1995) 11251.
[18] I. Shigeru, Y. Kazuo, U. Toshiuki, K. Masaki, N. Tsutomu, W.
Shigeomi, Jpn. Kokai Tokyo Koho, JP 02,129,129,171 (1990); Chem.
Abstr. (1990) 113, 172014a.
3.3.2. 3-Amino-4-trifluoromethyl-6-p-chloro
phenyl-N-methyl pyrazole[3,4-b] pyridine (5b)
Yield 49%, mp 202 8C, IR (KBr): 3310, 3250, 1240,
[19] H. Masataka, W. Junichi, K. Yasuo, S. Koichi, N. Tsutomu,
W. Shigeomi, Jpn. Kokai Tokyo Koho, JP 0,253,775 (1990); Chem.
Abstr. (1990) 113, 78374w.
1150 cmÀ1. H NMR (CDCl3): d 4.00 (s, 3H, CH3); 4.25
1
(s, br, 2H, –NH2); 7.45 (d, 2H, ArH); 7.6 (s, 1H, H–C(5)); 8.1
(d, 2H, ArH) ppm. MS: m/z 326 (Mþ, base peak); 228, 163,
95, 77; analysis: calcd. for C14H10ClF3N4: C, 51.47; H, 3.08;
N, 17.14%. Found: C, 51.32; H, 2.74; N, 17.02%.
[20] V.V. Alekseev, K.N. Zelenin, S.I. Yakimovich, Zh. Org. Khim. 937
(1995) 31 (Russian); Chem. Abstr. (1995) 124, pr. 260918f.
[21] P.N. Kondratev, Z.E. Skryabina, V.L. Saloutin, K.L. Pashkevich,
N.A. Klyuev, V.G.G. Aleksandro, Izv. Akd. NaukUSSR, Ser. Khim.
(1990) 640; Chem. Abstr. (1990) 113, 132071k.
[22] E.F.B. Mara, C. Gunter, A.P.M. Marcos, J. Heterocyclic Chem. 30
(1993) 1159.
Acknowledgements
[23] H.G. Bonacroso, A.D. Wastowski, N. Zanatta, M.A.P. Martins, J.A.
Naue, J. Fluorine Chem. 92 (1998) 23.
We thank Dr. K.V. Raghavan, Director, IICT, Hyderabad,
for constant encouragement.
[24] K.I. Pashkevich, V.I. Filyakova, O.A. Kuzznetsova, Izv. Akd.
NaukUSSR, Ser. Khim. (1996) 12, 3019; Chem. Abstr. (1996) 126,
264037g.
[25] B. Jiang, Y.-Y. Xu, J. Yang, J. Fluorine Chem. 67 (1994) 83.
[26] H.-B. Yu, W.-Y. Huang, J. Fluorine Chem. 84 (1997) 65.
[27] H.-B. Yu, W.-Y. Huang, J. Fluorine Chem. 87 (1998) 69.
[28] B. Narsaiah, A. Sivaprasad, R.V. Venkataratnam, OPPI Briefs 25
(1993) 116.
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