[4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-urea → [4-(2-Phenyl-2-o-tolyl-ethyl)-pyridin-2-yl]-urea

HRID 1023439Notes

Reaction equation

HRID 1023439 reaction equation
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>CO.C(Cl)Cl.[Pd]>[C:1]1([CH:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]([NH2:18])=[O:17])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 69083977[4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-ureaHCID 178418361HCID 178418361, compound

Product 1

HCID 69675800[4-(2-Phenyl-2-o-tolyl-ethyl)-pyridin-2-yl]-ureaYield 14%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

[4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-urea (140 mg, 0.43 mmol) is dissolved in methanol (2 mL) and DCM (2 mL). Then 5% palladium on carbon (90 mg, 0.043 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 Gilson preparative HPLC affords 20 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 Gilson preparative HPLC

Sources & evidence

ORD record
ord-d68d4513a52846dc93f7ff3d5378bc9d
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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