Azidobenzene → 1-Phenyltriazolylmethyl-3-methoxypyridine-2-one

HRID 539525

反応式

HRID 539525 の反応式
[CH2:1]([N:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH3:11])[C:5]1=[O:12])[C:2]#[CH:3].[C:13]1([N:19]=[N+:20]=[N-:21])[CH:18]=[CH:17]C=CC=1.CCN(C(C)C)[CH:25]([CH3:27])[CH3:26]>C1COCC1.C(Cl)Cl.[Cu]I>[C:1]1([N:4]2[CH:9]=[CH:8][C:7]([CH2:17][C:18]3[N:21]=[N:20][NH:19][CH:13]=3)=[C:6]([O:10][CH3:11])[C:5]2=[O:12])[CH:27]=[CH:25][CH:26]=[CH:3][CH:2]=1

参加物

7

反応物 3

HCID 69319AzidobenzeneHCID 81531DiisopropylethylamineHCID 71655522HCID 71655522、化合物

生成物 1

HCID 1784876421-Phenyltriazolylmethyl-3-methoxypyridine-2-one収率 92%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

150 (0.32 g, 1.951 mmol) and phenylazide (0.348 g, 2.926 mmol) were dissolved in anhydrous THF (10 mL) and stirred under argon at room temperature. Copper (I) iodide (0.011 g, 0.07 mmol) and Hunig's base (0.1 mL) were then added to the reaction mixture, and stirring continued for 4 h. The reaction mixture was diluted with CH2Cl2 (40 mL) and washed with 1:4 NH4OH/saturated NH4Cl (3×30 mL) and saturated NH4Cl (30 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was triturated with hexanes to give 510 mg (92%) of white solid 151a. 1H NMR (CDCl3, 400 MHz) δ 3.58 (3H, s), 5.11 (2H, s), 5.93 (1H, t, J=7.6), 6.42 (1H, d, J=7.2), 7.07 (1H, d, J=6.4), 7.16-7.20 (1H, m), 7.26 (2H, t, J=7.6), 7.49 (2H, d, J=8.0); 13C NMR (CDCl3, 100 MHz) δ 44.2, 55.2, 104.7, 112.0, 119.7, 121.8, 127.9, 128.1, 129.0, 136.2, 142.8, 149.3, 157.2. HRMS (EI) calcd for C15H14N4O2 [M]+ 282.1117. found 282.1115.

後処理

  1. stirringstirring
  2. washwashed with 1:4 NH4OH/saturated NH4Cl (3×30 mL) and saturated NH4Cl (30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was triturated with hexanes

出典と根拠

ORDレコード
ord-9bf95ba9cb8a4f1ca877deefdf743549
出典データセット
uspto-grants-2014_10
特許番号
US08871728B2

関連ノート

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