تفاعل #62209

ord-fbfc539e405f4b0a87a9c6ec5d541498

معادلة التفاعل

COc1ccc(C#Cc2ccncc2)cc1
4-(2-(4-methoxyphenyl)ethynyl)pyridine
C[Si](C)(C)N=[N+]=[N-]
trimethylsilylazide
COc1ccc(-c2[nH]nnc2-c2ccncc2)cc1
solid
المردود 53.0%
COc1ccc(-c2[nH]nnc2-c2ccncc2)cc1
4-(5-(4-methoxyphenyl)-1,2,3-triazol-4-yl)pyridine
المردود 53.0%

الكواشف

لا شيء

ظروف التفاعل

درجة الحرارة
150°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىThe mixture was chromatographed on silica using an ethyl acetate-hexanes gradient

الإجراء التجريبي

4-(2-(4-methoxyphenyl)ethynyl)pyridine (1.48 g, 7.1 mmol) and trimethylsilylazide (2.5 g, 21.3 mmol) were combined in a sealed tube which was heated 48 h in a 150° C. oil bath. The mixture was chromatographed on silica using an ethyl acetate-hexanes gradient giving a yellow solid (950 mg, 53%). 1H NMR (CDCl3, 400 mHz) δ 8.50 (d, 2H, J=5.8 Hz), 7.60 (d, 2H, J=5.8 Hz), 7.36 (d, 2H, J=8.7 Hz), 6.92 (d, 2H, J=8.7 Hz), 3.81 (s, 3H), 2.80 (br, 1H). MS (AP+) m/e 253 (MH+).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07429665B2uspto-grants-2008_09