Triethylamine → 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

HRID 1398180Notes

Reaction equation

HRID 1398180 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([CH3:13])=[N:9]2)=[C:4]([O:14][CH3:15])[CH:3]=1.[CH2:16]([OH:22])[CH2:17][CH2:18][CH2:19][C:20]#[CH:21].C(N(CC)CC)C>C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:15][O:14][C:4]1[CH:3]=[C:2]([C:21]#[C:20][CH2:19][CH2:18][CH2:17][CH2:16][OH:22])[CH:7]=[CH:6][C:5]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 702345-Hexyn-1-olHCID 666089771-(4-bromo-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole

Product 1

HCID 666088346-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-(4-bromo-2-methoxyphenyl)-3-methyl-1H-1,2,4-triazole (3.00 g), 5-hexyn-1-ol (2.45 mL), dichlorobis(triphenylphosphine)palladium(II) (786 mg), copper(I) iodide (213 mg) and triethylamine (110 mL) was stirred at 70° C. for 14 hr, allowed to cool to room temperature, and diluted with ethyl acetate, and the mixture was filtered through celite. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.80 g).

Workup

  1. temperatureto cool to room temperature
  2. filtrationthe mixture was filtered through celite
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-f3ecba20eb1a42cd96adf38eca5268e5
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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