Polymer support assisted selective functionalization of Azoles using a palladium-catalyzed coupling reaction

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3111-3113

  Kondo, Yoshinori ^a   Komine, Takashi ^a   Sakamoto, Takao ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010597557     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000183u     Document Type: Article

References (46)

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45. 3 (107.1 mg, 0.33 mmol) were placed in a 50 mL round-bottom flask and then dried in vacuo for 1 h. N-Methylimidazole (0.13 mL, 1.63 mmol) and DMF (4 mL) were then added, and the resulting mixture was stirred under argon at 120°C for 16 h. After cooling, the mixture was filtered and washed with THF and MeOH for several cycles. The resin was treated with NaOMe in MeOH (0.4 mL, 2.0 mmol) and THF-MeOH (2:1, 12 mL), and the mixture was stirred at room temperature for 6 h. Methyl 4-(1-methyl-1H-imidazol-5-yl)benzoate (47.9 mg, 67%) was then obtained.
46. 3 (172.8 mg, 0.53 mmol), and CuI (609.7 mg, 3.2 mmol) were placed in a 50 mL round-bottom flask and then dried in vacuo for 1 h. N-Methylimidazole (0.13 mL, 1.63 mmol) and DMF (6 mL) were then added, and the resulting mixture was stirred under argon at 120°C for 16 h. After cooling, the mixture was filtered and washed with THF and MeOH for several cycles. The resin was treated with NaOMe in MeOH (0.4 mL, 2.0 mmol) and THF-MeOH (2:1, 12 mL), and the mixture was stirred at room temperature for 6 h. Methyl 4-(1-methyl-1H-imidazol-2-yl)benzoate (56.3 mg, 49%) was then obtained.