RSC Advances
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DOI: 10.1039/C4RA11183D
1-(4-Chlorophenyl)-1H-imidazole 3e7. Brown oil; 1H NMR
(400 MHz, DMSOꢀd6): δ 8.28 (s, 1H), 7.76 (s, 1H), 7.71 (d, J =
7.2 Hz, 2H), 7.58 (d, J = 6.8 Hz, 2H), 7.13 (s, 1H); GCꢀMS (EI)
[M]+: m/z calcd. for C9H7ClN2: 178.0, found: 178.
4-Methoxyphenyl phenyl sulfide 5a32. Colorless oil; 1H NMR
(400 MHz, CDCl3): δ 7.41 (d, J = 8.8 Hz, 2H), 7.27ꢀ7.08 (m, 5H),
6.88 ( J = 8.8 Hz, 2H), 3.80 (s, 3H); GCꢀMS (EI) [M]+: m/z calcd.
for C13H12OS: 216.1, found: 216.
1
1-(4-(Trifluoromethylphenyl)-1H-imidazole 3f7. Brown solid;
(4-Nitrophenyl)(phenyl)sulfane 5b32. Colorless oil; H NMR
m.p.: 69–71
℃
. 1H NMR (400MHz, DMSO): δ 7.93 (s, 1H), 7.76
(400 MHz, CDCl3): δ 8.07 (dd, J = 8.8, 2.4 Hz, 2H), 7.55ꢀ7.53 (m,
2H), 7.47ꢀ7.45 (m, 3H), 7.16 (dd, J = 8.8, 2.8 Hz, 2H); GCꢀMS
(EI) [M]+: m/z calcd. for C12H9NO2S: 231.0, found: 231.
(d, J = 8 .0 Hz, 2H), 7.53 (d, J = 8.0 Hz, 2H), 7.34 (s, 1H), 7.27 (s,
1H); GCꢀMS (EI) [M]+: m/z calcd. for C10H7F3N2: 212.1, found:
212.
1
4-Chlorophenyl phenyl sulfide 5c32. Colorless oil; H NMR
1-Phenyl-1H-imidazole 3g19. Slightly yellow oil; 1H NMR
(400 MHz, DMSOꢀd6): δ 8.27 (s, 1H), 7.75 (s, 1H), 7.66 (d, J = 6
Hz, 2H), 7.53 (t, J = 6 Hz, 2H), 7.38 (t, J = 5.6 Hz, 1H), 7.13 (s,
1H); GCꢀMS (EI) [M]+: m/z calcd. for C9H8N2: 144.1, found:
144.
(400 MHz, CDCl3): δ 7.35ꢀ7.23 (m, 9H). GCꢀMS (EI) [M]+: m/z
calcd. for C12H9ClS: 220.0, found: 220.
(Naphthalen-2-yl)(phenyl)sulfane 5d32. Colorless oil; 1H
NMR (400 MHz, CDCl3): δ 7.83ꢀ7.76 (m, 2H), 7.74ꢀ7.70 (m, 2H),
7.48ꢀ7.44 (m, 2H), 7.41ꢀ7.36 (m, 2H), 7.32ꢀ7.23 (m, 4H); GCꢀMS
(EI) [M]+: m/z calcd. for C18H14S: 262.1, found: 262.
1
1-(1H-Pyrazol-4-yl)-1H-imidazole 3h7. Brown oil; H NMR
(400 MHz, DMSOꢀd6): δ 8.42 (s, 1H), 7.93 (t, J = 7.2 Hz, 4H),
7.17 (s, 1H); GCꢀMS (EI) [M]+: m/z calcd. for C6H6N4: 134.1,
found: 134.
Phenyl(o-tolyl)sulfane 5e36. Colorless oil; 1H NMR (400 MHz,
CDCl3): δ 2.42 (s, 3H), 7.16ꢀ 7.37 (m, 9H). GCꢀMS (EI) [M]+:
m/z calcd. for C13H12S: 200.1, found: 200.
1-(4-Methoxyphenyl)-4-methyl-1H-imidazole 3i9c. White
needles; m.p.: 78–80
℃.
1 H NMR (400 MHz, DMSOꢀd6): δ 7.64
4-(Phenylthio)-1H-pyrazole 5f36. Colorless oil; 1H NMR (400
MHz, CDCl3): δ 6.95ꢀ7.07 (m, 3H), 7.09ꢀ7.19 (m, 2H), 7.68 (s,
2H); GCꢀMS (EI) [M]+: m/z calcd. for C9H8N2S: 176.0, found:
176.
(s, 1H), 7.27 (d, J = 9.5, 2H), 6.97 (d, J = 9.2 H), 6.82 (s, 1H)
3.84 (s, 3H) 2.29 (s, 3H); GCꢀMS (EI) [M]+: m/z calcd. for
C11H12N2O: 188.1, found: 188.
1-(4-Methoxyphenyl)-1H-indole 3j9d. White crystalline solid;
mp 59−61 °C. 1H NMR (400 MHz, DMSOꢀd6): δ 7.61(d, J = 7.32
Hz, 1 H), 7.39ꢀ7.36 (m, 3 H), 7.23ꢀ7.20 (m, 1 H), 7.15ꢀ7.06 (m, 2
H), 6.99ꢀ6.96 (m, 2 H), 6.58ꢀ6.57 (d, J = 2.93 Hz, 1 H), 3.85 (s, 3
H); GCꢀMS (EI) [M]+: m/z calcd. for C15H13NO: 223.1, found:
223.
Diphenyl sulfide 5g36. Colorless oil; 1H NMR (400 MHz,
CDCl3): δ 7.37ꢀ7.16 (m, 10H). GCꢀMS (EI) [M]+: m/z calcd. for
C12H10S: 186.1, found: 186.
Nilotinib intermediate 731. Colorless oil ;1H NMR (400 MHz,
CDCl3): δ 7.79 (s, H), 7.01 (s, H), (m, 2H), 6.94 (s, 1H), 6.85 (s,
1H), 6.79 (s, 1H), 4.18 (b, 2H), 2.30 (s, 3H); GCꢀMS (EI) [M]+:
m/z calcd. for C11H8F3N3O2: 241.0, found: 241.
1-(4-Methoxyphenyl)pyrrolidine 3k9d. Yellow solid; m.p.:
1
46–48
℃
. H NMR (400 MHz, DMSOꢀd6): δ 1.97ꢀ2.01 (m, 4H),
2.22ꢀ3.26 (m, 4H), 3.74 (s, 3H), 6.58ꢀ6.61 (d, 2H), 6.81ꢀ6.85 (m,
2H); GCꢀMS (EI) [M]+: m/z calcd. for C11H15NO: 177.1, found:
177.
Acknowledgments
This work was supported by Science and Technology Plan of
Zhejiang Province (No. 2014C31153), the National Natural
Science Foundation of China (No. 21376058, 21302171) and
Zhejiang Provincial Natural Science Foundation of China (No.
LZ13B020001).
1-(4-Methoxyphenyl)-1H-benzo[d]imidazol-2-amine
Yellow solid; m.p.: 195–197
. 1H NMR (400 MHz, DMSOꢀd6):
3l30.
℃
δ 7.40 (d, J = 6.8 Hz, 2H), 7.23 (d, J = 6 Hz, 1H), 7.16 (d, J = 4
Hz, 2H), 7.02 (t, J = 6.8 Hz, 1H), 6.88 (t, J = 8 Hz, 1H), 6.80 (d, J
= 6.4 Hz, 1H), 6.21 (s, 2H); GCꢀMS (EI) [M]+: m/z calcd. for
C14H13N3O: 239.1, found: 239.
Notes and references
General procedure for C-S cross-coupling reactions
A mixture of aryl halide (1 mmol), phenyl disulfide (0.6 mmol),
1
(a) K.ꢀG. Liu, A. J. Robichaud, R. C. Bernotas, Y. Yan, J. R. Lo, M.
ꢀY. Zhang, Z. A. Hughes, C. Huselton, G.ꢀM. Zhang, J.ꢀY. Zhang, D.
M. Kowal, D. L. Smith, L. E. Schechter and T. A. Comery, J. Med.
Chem. 2010, 53, 7639; (b) A. V. Ivachtchenko, E. S. Golovina, M. G.
Kadieva, V. M. Kysil, O. D. Mitkin, S. E. Tkachenko and I. M. Okun,
J. Med. Chem., 2011, 54, 8161; (c) C. Shen, P.ꢀF. Zhang, Q. Sun, S.
ꢀQ. Bai, T. S. Andy Hor and X.ꢀG. Liu, Chem. Soc. Rev., 2014, DOI:
DOI: 10.1039/c4cs00239c
CuI (0.1 mmol),
Dꢀglucosamine (0.1 mmol), and 3 mL of
DMSOꢀH2O (1:1) in a tube was heated to at 80ꢀ110 °C under air.
Monitoring of the reaction, workup procedure, and purification of
the CꢀS crossꢀcoupled products were performed as described for
the CꢀN crossꢀcoupling reactions. All compounds were
characterized by 1H NMR and GCꢀMS spectroscopy, which were
consistent with those reported in the literature.
2
A. Bhunia, S. R. Yetra and A. T. Biju, Chem. Soc. Rev., 2012, 41,
3140ꢀ3152.
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