2,2'-Bipyridine → 3-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol

HRID 340853

반응식

HRID 340853 반응식
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1.[N:14]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)=[N+:15]=[N-:16].N1C=CC=CC=1C1C=CC=CN=1>CN(C=O)C.CCOC(C)=O>[OH:23][C:19]1[CH:18]=[C:17]([N:14]2[CH:3]=[C:4]([C:5]3[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=3)[N:16]=[N:15]2)[CH:22]=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 14742,2'-BipyridineHCID 113670133-AzidophenolHCID 220877193-((Trimethylsilyl)ethynyl)phenol

생성물 1

HCID 167211153-[1-(3-hydroxyphenyl)-1H-1,2,3-triazol-4-yl]phenol수율 70%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To 3-TMSE-phenol (4.0 g, 21.02 mmol) in 35 mL of DMF were added 3-azidophenol (3.41 g, 25.2 mmol), CuBr (153 mg, 1.05 mmol), and 2,2′-bipyridyl (328 mg, 2.10 mmol). The mixture was heated at 80° C. for 24 h, cooled to room temperature, then diluted with 250 mL of EtOAc. The combined organic mixture washed with water, and dried over MgSO4. Solvents were removed by rotary evaporation, and the residue was recrystallized in acetic acid/water to give 3.70 g (70% yield) of a brown crystalline solid. 1H NMR (MeOD-d4, 300 MHz, ppm): 8.80 (s, 1H, triazol-H), 7.43-7.26 (m, 6H, Ar—H), 6.95-6.91 (m, 1H, Ar—H), 6.84-6.83 (m, 1H, Ar—H). 13C NMR (MeOD-d4, 75 MHz, ppm): 158.6, 157.7, 148.1, 137.9, 131.1, 130.4, 129.7, 118.8, 116.7, 115.6, 115.1, 112.1, 110.7, 107.1.

후처리

  1. temperaturecooled to room temperature
  2. washThe combined organic mixture washed with water
  3. dry with materialdried over MgSO4
  4. customSolvents were removed by rotary evaporation
  5. customthe residue was recrystallized in acetic acid/water

출처 및 근거

ORD 기록
ord-80c982d2787b48b6a578d815f090cc87
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895688B2

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