반응 #62210

반응 방정식

4-(2-methyl-5-(pyridin-4-yl)-2H-1,2,3-triazol-4-yl)phenol

2-(chloromethyl)quinoline hydrochloride

cesium carbonate

→

solid

수율 80.0%

2-((4-(2-methyl-5-(pyridin-4-yl)-2H-1,2,3-triazol-4-yl)phenoxy)methyl)quinoline

수율 80.0%

용매

dimethylformamide

반응 조건

후처리

1. 1
   여과filtered
2. 2
   농축the filtrate concentrated
3. 3
   기타chromatographed on silica
4. 4
   세척eluted with ethyl acetate-hexanes providing material
5. 5
   workup.ADDITIONcontaining starting phenol
6. 6
   workup.DISSOLUTIONThis was dissolved in ethyl acetate
7. 7
   세척washed with aqueous NaOH
8. 8
   기타dried
9. 9
   농축concentrated

실험 절차

A mixture of 4-(2-methyl-5-(pyridin-4-yl)-2H-1,2,3-triazol-4-yl)phenol (80 mg, 0.32 mmol), 2-(chloromethyl)quinoline hydrochloride (71 mg, 0.33 mg), and cesium carbonate (414 mg, 1.27 mmol) in dimethylformamide was heated at 65° C. for 20 h, filtered, the filtrate concentrated and chromatographed on silica eluted with ethyl acetate-hexanes providing material containing starting phenol. This was dissolved in ethyl acetate, washed with aqueous NaOH, dried and concentrated giving a colorless solid (100 mg, 80%). 1H NMR (CDCl3, 400 mHz) δ 8.56 (d, 2H, J=6.2 Hz), 8.24 (d,1H, J=8.3 Hz), 8.12 (d, 1H, J=8.3 Hz), 7.85 (d, 1H, J=8.3 Hz), 7.75 (ddd, 1H, J=8.5, 7, 1.6 Hz), 7.70 (d, 1H, J=8.7 Hz), 7.65 (d, 2H, J=6.2 Hz), 7.57 (m, 1H), 7.41 (m, 2H), 7.08 (m, 2H), 5.45 (s, 2H), 4.27 (s, 3H). MS (AP+) m/e 394 (MH+).

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