Triethylamine → 3-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine

HRID 349220Notes

Reaction equation

HRID 349220 reaction equation
I[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]=[C:12]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=3)[O:13][CH:14]=2)=[CH:6][CH:7]=1.[CH2:27]([N:31]1[CH:35]=[CH:34][N:33]=[N:32]1)[CH2:28][C:29]#[CH:30].C(N(CC)CC)C.C(OCC)(=O)C>C1COCC1.[Cu](I)I.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>[N:31]1([CH2:27][CH2:28][C:29]#[C:30][C:2]2[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]3[N:11]=[C:12]([CH:15]=[CH:16][C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)[O:13][CH:14]=3)=[CH:6][CH:7]=2)[CH:35]=[CH:34][N:33]=[N:32]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 184535221-But-3-ynyl-1H-[1,2,3]triazoleHCID 866009353-Iodo-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine

Product 1

HCID 694859873-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-Iodo-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine (0.114 g, 0.25 mmol), 1-but-3-ynyl-1H-[1,2,3]triazole (0.040 g, 0.30 mmol) and triethyl amine (NEt3) (0.125 ml) are dissolved in THF (1 ml) and copper iodide (CuI) (0.0048 g, 0.025 mmol) is added under stirring. After passing a stream of argon through the mixture for 10 min bis(triphenylphosphine)palladium(II) dichloride (0.088 g, 0.0125 mmol) is added and stirring is continued for 3 h at r.t. Ethyl acetate (30 ml) is added; the mixture is washed with saturated ammonium chloride (NH4Cl) and brine, dried over MgSO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (ethyl acetate/hexanes 1:3->ethyl acetate (100%)) yielding 3-(4-[1,2,3]triazol-1-yl-but-1-ynyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine as a colorless solid. Yield 93 mg (64%).

Workup

  1. customfor 10 min
  2. additionis added
  3. stirringstirring
  4. washthe mixture is washed with saturated ammonium chloride (NH4Cl) and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (ethyl acetate/hexanes 1:3->ethyl acetate (100%))

Sources & evidence

ORD record
ord-fc5a81b608a74dc6b4a90b0767c93a80
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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