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

HRID 539525

반응식

HRID 539525 반응식
[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

참가 물질

7

반응물 3

HCID 69319AzidobenzeneHCID 81531DiisopropylethylamineHCID 71655522HCID 71655522, 화합물

생성물 1

HCID 1784876421-Phenyltriazolylmethyl-3-methoxypyridine-2-one수율 92%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9bf95ba9cb8a4f1ca877deefdf743549
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871728B2

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