Triethylamine → HCID 18388840, compound

HRID 2296996Notes

Reaction equation

HRID 2296996 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[CH2:7][N:8]1[C:12]([O:13][CH3:14])=[N:11][N:10]([CH3:15])[C:9]1=[O:16].[CH2:19]([C:26]#[CH:27])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C(#N)C.C(OC(C)(C)C)(C)(C)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>[C:20]1([CH2:19][C:26]#[C:27][C:2]2[CH:3]=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=2)[CH2:7][N:8]2[C:12]([O:13][CH3:14])=[N:11][N:10]([CH3:15])[C:9]2=[O:16])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 575753BenzylacetyleneHCID 120565184-(5-bromo-2-methylbenzyl)-5-methoxy-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one

Product 1

HCID 18388840HCID 18388840, compoundYield 51.4%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolventHCID 22541Di-tert-butyl etherSolvent

Procedure

A mixture of 437 mg (1.4 mmol) of 4-(5-bromo-2-methylbenzyl)-5-methoxy-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 299 of the present invention), 325 mg (2.8 mol) of benzylacetylene, 41 mg (0.058 mmol) of PdCl2(PPh3)2, 33 mg (0.17 mmol) of copper (I) iodide, 82 mg (0.31 mmol) of triphenylphosphine and 0.80 g of triethylamine in 4 ml of acetonitrile was heated under reflux under an atmosphere of nitrogen for 9 hours. After cooling to room temperature, the reaction mixture was diluted with tert-butyl ether, washed with water, dried and concentrated. The residue was subjected to silica gel column chromatography (eluted with hexane:ethyl acetate=2:1) to obtain 0.25 g of 4-{5-(3-phenyl-l-propynyl)-2-methylbenzyl}-5-methoxy-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one (the compound 535 of the present invention).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an atmosphere of nitrogen for 9 hours
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. washThe residue was subjected to silica gel column chromatography (eluted with hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-9c350b4a835b4ce1abe2a8c664d37589
Source dataset
uspto-grants-2002_12
Patent number
US06489487B1

Reaction notes

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