HCID 9815076, compound → HCID 9900281, compound

HRID 1823852Notes

Reaction equation

HRID 1823852 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[N:8]=1>C(O)C.[Pd]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]=[C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[Cl:1])[O:11][N:10]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 9815076HCID 9815076, compound

Product 1

HCID 9900281HCID 9900281, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(3-chloro-thiophen-2-yl)-3-(4-nitro-phenyl)-[1,2,4]-oxadiazole and Pd/C (30 mg) in ethanol (30 mL) under hydrogen (46 psi) was shaken for 6 h. After filtration, the filtrate was concentrated and applied to small column chromatography (hexane:ethyl acetate, 5:1) to yield 18 mg (25%) of the title compound. 1H NMR (CDCl3): 7.98 (d, J=8.7 Hz, 2H), 7.60 (d, J=5.1 Hz, 1H), 7.14 (d, J=5.1 Hz, 2H), 6.78 (d, J=8.7 Hz, 1H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-11e3d7d56390423aafd594c5eebcdeb2
Source dataset
uspto-grants-2006_05
Patent number
US07041685B2

Reaction notes

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