反応 #2468982

反応方程式

N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide

N,N-diisopropylethylamine

1-(2-azidoethyl)-4-fluorobenzene

→

title compound

収率 55.0%

N-benzyl-2-(1-(4-fluorophenethyl)-1H-1,2,3-triazol-4-yl)-4-methylthiazole-5-carboxamide

収率 55.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   濃縮then concentrated in vacuo
2. 2
   その他The residue was purified by column chromatography (ethyl acetate:hexanes, 1:1)

実験手順

To a solution of N-benzyl-2-ethynyl-4-methylthiazole-5-carboxamide (0.10 g, 0.39 mmol) in tetrahydrofuran (5 mL) was added copper(I) iodide (0.002 g, 0.008 mmol), N,N-diisopropylethylamine (0.082 mL, 0.47 mmol) and 1-(2-azidoethyl)-4-fluorobenzene (0.077 g, 0.47 mmol). The reaction mixture was stirred at ambient temperature for 17 hours then concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexanes, 1:1) to afford the title compound as a white solid (0.090 g, 55%): mp 181-182° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.84 (s, 1H), 7.38-7.24 (m, 5H), 7.09-6.99 (m, 2H), 6.95-6.85 (m, 2H), 6.23 (t, J=5.6 Hz, 1H), 4.61-4.56 (m, 4H), 3.20 (t, J=7.1 Hz, 2H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.9, 161.6, 157.9, 156.7, 142.5, 137.8, 132.2, 130.1, 128.8, 127.8, 127.7, 124.8, 121.8, 115.9, 52.0, 44.2, 35.7, 17.3; MS (ES+) m/z 422.3 (M+1).

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