Cesium carbonate → (2-(2H-1,2,3-Triazol-2-YL)phenyl)methanol

HRID 41582

Reaction equation

HRID 41582 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][OH:9].[NH:10]1[CH:14]=[CH:13][N:12]=[N:11]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.[Cu]I.CN[C@@H]1CCCC[C@H]1NC>[N:10]1[N:11]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[CH2:8][OH:9])[N:12]=[CH:13][CH:14]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 1076292-Iodobenzylic alcoholHCID 178418936HCID 178418936, compound

Product 1

HCID 67251671(2-(2H-1,2,3-Triazol-2-YL)phenyl)methanolYield 130%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

To a mixture of (2-iodophenyl)methanol [5159-41-1] (1.50 g, 6.41 mmol), 1H-1,2,3-triazole (0.797 g, 11.54 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine [68737-65-5] (0.091 g, 0.641 mmol) and Cs2CO3 (3.76 g, 11.54 mmol) in DMF (15 mL), CuI (0.61 g, 3.20 mmol) was added and the reaction mixture was stirred for 20 min at 120° C. and 15 min at 160° C. in the microwave. The reaction mixture was cooled to rt and filtered to remove the solids. The filtrate was concentrated under reduced pressure. The residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane) to yield the title compound (1.46 g, 64%). [1H NMR (400 MHz, DMSO-d6) ♀ ppm 8.10 (s, 2H), 7.74 (d, J=7.53 Hz, 1H), 7.61 (dd, J=8.03, 1.25 Hz, 1H), 7.52 (td, J=7.53, 1.25 Hz, 1H), 7.44 (m, 1H), 5.26 (t, J=5.40 Hz, 1H), 4.59 (d, J=5.02 Hz, 2H); LCMS RtA=0.68, [M+H]+=176.1].

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. customto remove the solids
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by flash-column chromatography over silicagel (eluent: gradient 10%-100% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-e73e2ef4f7bb44c99e97196b1224ac4c
Source dataset
uspto-grants-2013_09
Patent number
US08530648B2

Linked notes

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