The successive substitution of halogens in 4-chloro-6-iodoquinoline by aryl groups in cross-coupling reactions with arylboronic acids

Tetrahedron Letters

Volumn 43, Issue 40, 2002, Pages 7267-7270

  Tsvetkov, Alexey V ^a   Latyshev, Gennadij V ^a   Lukashev, Nikolai V ^a   Beletskaya, Irina P ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

Author keywords

Diarylquinolines; Palladium; Successive cross coupling; Suzuki reaction

Indexed keywords

4 CHLORO 6 IODOQUINOLINE; BORONIC ACID DERIVATIVE; CHLORINE; HALOGEN; IODINE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; ATOMIC PARTICLE; CHEMICAL PARAMETERS; CHEMICAL PROCEDURES; METHODOLOGY; SYNTHESIS;

LATEOLABRAX JAPONICUS;

EID: 0037201098     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01516-2     Document Type: Article

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15. 3 (1.032 mmol), 1.5 ml of dioxane and 0.5 ml of water were refluxed under argon with 3.4 μmol (2 mol%) of catalyst. The reaction was monitored by TLC. After the reaction was finished, the second boronic acid (0.224 mmol, 1.3 equiv.) was added to the reaction mixture. After the second reaction was finished the reaction mixture was diluted with ether, filtered through silica gel, evaporated in vacuo, and purified by column chromatography using silica gel (ether-hexane 1:1).
16. 3, 400 MHz) of coupling products. Compound 2: δ 3.86 (s, 3H), 7.02 (m, 2H), 7.47 (d, J (H,H)=4.7 Hz, 1H), 7.66 (m, 2H), 7.98 (dd, J (H,H)=8.8 Hz, J (H,H)=2.1 Hz, 1H), 8.15 (d, J (H,H)=8.8 Hz, 1H), 8.33 (d, J (H,H)=2.1 Hz, 1H), 8.73 (d, J (H,H)=4.7 Hz, 1H). Compound 3: δ 2.44 (s, 3H), 3.81 (s, 3H), 6.95 (m, 2H), 7.31 (m, 3H), 7.42 (m, 2H), 7.52 (m, 2H), 7.92 (dd, J (H,H)=8.8 Hz, J (H,H)=2.1 Hz, 1H), 8.06 (d, J (H,H)=2.1 Hz, 1H), 8.20 (d, J (H,H)=8.8 Hz, 1H), 8.87 (d, J (H,H)=4.7 Hz, 1H). Compound 4: δ 2.35 (s, 3H), 2.43 (s, 3H), 7.21 (m, 2H), 7.29 (m, 3H), 7.42 (m, 2H), 7.47 (m, 2H), 7.93 (dd, J (H,H)=8.8 Hz, J (H,H)=2.1 Hz, 1H), 8.09 (d, J (H,H)=2.1 Hz, 1H), 8.19 (d, J (H,H)=8.8 Hz, 1H), 8.86 (d, J (H,H)=4.7 Hz, 1H). Compound 5: δ 2.46 (s, 3H), 7.36 (m, 7H), 7.50 (m, 2H), 7.90 (dd, J (H,H)=8.8 Hz, J (H,H)=2.1 Hz, 1H), 8.07 (d, J (H,H)=2.1 Hz, 1H), 8.21 (d, J (H,H)=8.8 Hz, 1H), 8.91 (d, J (H,H)=4.4 Hz, 1H). Compound 6: δ 7.29 (d, J (H,H)=4.4, 1H), 7.36 (m, 2H), 7.43 (m, 2H), 7.48 (m, 4H), 7.91 (dd, J (H,H)=8.8 Hz, J (H,H)=2.1 Hz, 1H), 7.96 (d, J (H,H)=2.1 Hz, 1H), 8.24 (d, J (H,H)=8.8 Hz, 1H), 8.92 (d, J (H,H)=4.4 Hz, 1H).