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

HRID 340853

Reaction equation

HRID 340853 reaction equation
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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-80c982d2787b48b6a578d815f090cc87
Source dataset
uspto-grants-2014_11
Patent number
US08895688B2

Linked notes

Loading…