7-Chloroquinoline: a versatile intermediate for the synthesis of 7-substituted quinolines

Tetrahedron Letters

Volumn 50, Issue 35, 2009, Pages 4989-4993

  Hirner, Joshua J ^a   Zacuto, Michael J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; QUINOLINE DERIVATIVE; REAGENT;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 67650084295     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.077     Document Type: Article

References (34)

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22. The ratio of 4:5 was determined using HPLC by comparison of the area under the curve for each compound in the reaction mixture. This ratio was then corrected with the extinction coefficient of each component as determined from independently prepared samples of known concentration. Conversion values were calculated as the ratio of (4+5):3, with correction by the extinction coefficient as above.
23. 7ClN calc'd [M+H] = 164.0267, found 164.0300.
24. 2 + ligands, including numerous triarylphosphines, SPhos and XPhos. Although Pd(0) complexes were active catalysts (entries 1-4), we focused on P(II) species due to their relative ease of handling in air.
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26. 2 = 8.4 Hz, 1H), 7.24-7.17 (m, 2H).
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29. 2 = 7.4 Hz, 2H), 1.37 (s, 9H).
30. 3) δ 152.3, 147.1, 136.0, 135.5, 130.3, 129.3, 127.3, 123.6, 118.4, 113.0.
31. 2 = 10.0 Hz, 1H), 4.29-4.20 (m, 1H), 3.81 (br s, 1H), 1.65-1.51 (m, 2H), 1.42-1.30 (m, 2H), 0.92 (t, J = 7.0 Hz, 3H).
32. 2 = 8.6 Hz, 1H), 7.30 (d, J = 8.6 Hz, 1H), 2.79 (t, J = 8.1 Hz, 2H), 1.84-1.77 (m, 2H), 1.49-1.41 (m, 2H), 0.98 (t, J = 7.4 Hz, 3H).
33. Interestingly, iPrMgCl was unreactive under these conditions. PhMgCl underwent a similar 1,2-addition as described in Eq. 3.
34. 3) δ 8.12 (d, J = 8.7 Hz, 1H), 7.85 (d, J = 8.4 Hz, 1H), 7.78-7.67 (m, 4H), 7.23-7.16 (m, 2H), 5.97-5.94 (m, 1H), 5.54-5.50 (m, 1H), 2.41-2.38 (m, 3H).