HCID 23076431, compound → HCID 69217575, compound

HRID 2221542Notes

Reaction equation

HRID 2221542 reaction equation
[CH2:1]([O:8][C:9]1[C:13](/[CH:14]=[CH:15]/[C:16]2[N:17]=[CH:18][S:19][CH:20]=2)=[CH:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH2:14][CH2:15][C:16]2[N:17]=[CH:18][S:19][CH:20]=2)=[CH:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23076431HCID 23076431, compound

Product 1

HCID 69217575HCID 69217575, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-[(E)-2-(3-Benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethenyl]-1,3-thiazole (0.81 g), 5% palladium on carbon (0.80 g) and tetrahydrofuran (80 mL) were subjected to catalytic reduction under a hydrogen atmosphere and atmospheric pressure. The catalyst was filtered off and the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:3, v/v) to give 4-[2-(3-benzyloxy-1-phenyl-1H-pyrazol-4-yl)ethyl]-1,3-thiazole as a colorless oil (0.58 g, yield 70%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. washeluted with ethyl acetate-hexane (1:3

Sources & evidence

ORD record
ord-4e627219ed024e21b809bff6801ba15b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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