HCID 69085911, compound → HCID 69084746, compound

HRID 1023443Notes

Reaction equation

HRID 1023443 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1.[H][H]>CO.C(Cl)Cl.[Pd]>[F:22][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 2

HCID 69085911HCID 69085911, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69084746HCID 69084746, compoundYield 33.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

{4-[2-(3-Trifluoromethyl-phenyl)-vinyl]-pyridin-2-yl}-urea (210 mg, 0.68 mmol) is dissolved in methanol (3 mL) and DCM (3 mL). Then 5% palladium on carbon (145 mg, 0.068 mmol) is added. The reaction is stirred for 16 hours under the hydrogen atmosphere. The palladium on carbon is filtered and the filtrate is concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 71 mg of the titled product.

Workup

  1. filtrationThe palladium on carbon is filtered
  2. concentrationthe filtrate is concentrated
  3. customto give the crude product
  4. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-a05ecfcd39374efc9099123c067916a5
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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