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

HRID 349222Notes

Reaction equation

HRID 349222 reaction equation
[N:1]1([CH2:6][CH2:7][C:8]#[C:9][C:10]2[N:11]=[N:12][C:13]([O:16][CH2:17][C:18]3[N:19]=[C:20]([CH:23]=[CH:24][C:25]4[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=4)[O:21][CH:22]=3)=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=[N:2]1>C(OCC)(=O)C.[Pd]>[N:1]1([CH2:6][CH2:7][CH:8]=[CH:9][C:10]2[N:11]=[N:12][C:13]([O:16][CH2:17][C:18]3[N:19]=[C:20]([CH:23]=[CH:24][C:25]4[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:29][CH:30]=4)[O:21][CH:22]=3)=[CH:14][CH:15]=2)[CH:5]=[CH:4][N:3]=[N:2]1

Participants

4

Reactant 1

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

Product 1

HCID 694867033-(4-[1,2,3]Triazol-1-yl-but-1-enyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-[1,2,3]Triazol-1-yl-but-1-ynyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine (0.047 g, 0.1 mmol) is dissolved in ethyl acetate (3 ml) and hydrogenated for 1 h at r.t. in the presence of palladium on charcoal (10%, 5 mg). After filtration and concentration in vacuo the residue yielded 3-(4-[1,2,3]triazol-1-yl-but-1-enyl)-6-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-pyridazine as an off-white solid. The raw product contained 60% product and 40% educt. The ratio was detected by HPLC-MS (High Performance Liquid Chromatography-Mass Spectrometry; Eluent: H2O/CH3CN, Gradient: in 20 minutes from 0% (volume to volume (v/v)) to 95% (v/v) CH3CN, UV-detection at 226 nm).

Workup

  1. filtrationAfter filtration and concentration in vacuo the residue

Sources & evidence

ORD record
ord-12bb6d3ac0364808897bf08231c492f8
Source dataset
uspto-grants-2007_02
Patent number
US07179812B2

Reaction notes

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