Regioselective synthesis of 1-arylindazoles via N-arylation of 3-trimethylsilylindazoles

Tetrahedron Letters

Volumn 46, Issue 21, 2005, Pages 3771-3774

  Hari, Yoshiyuki ^a   Shoji, Yoshimichi ^a   Aoyama, Toyohiko ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

Author keywords

Arylboronic acid; Indazoles; N Arylation; Regioselectivity; Silyl compounds

Indexed keywords

BENZENE; BORONIC ACID DERIVATIVE; COPPER; INDAZOLE DERIVATIVE; POTASSIUM DERIVATIVE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; ARYLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CROSS COUPLING REACTION; DRUG SYNTHESIS; ISOMER; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 17844386596     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.157     Document Type: Article

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16. 2Si: C, 72.13; H, 6.81; N, 10.52. Found: C, 71.99; H, 6.94; N, 10.18
17. 3) δ: 0.41 (9H, s), 3.71 (3H, s), 3.94 (3H, s), 6.42 (1H, d, J = 8 Hz), 6.70 (1H, d, J = 8 Hz), 7.44-7.56 (4H, m)
18. Under the same reaction conditions as shown in entry 2 of Table 1, the reaction of indazole with 4-tolylboronic acid has been reported to give a mixture of 1- and 2-(4-tolyl)indazole (9:2) in 88% yield. See Ref. 3
19. 18 mp 78°C)
20. 3) δ: 3.73 (3H, s), 3.94 (3H, s), 6.42 (1H, d, J = 8 Hz), 6.70 (1H, d, J = 8 Hz), 7.45 (1H, d, J = 9 Hz), 7.55 (1H, d, J = 9 Hz), 8.22 (1H, s)
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