HCID 86672052, compound → HCID 70816758, compound

HRID 1261764Notes

Reaction equation

HRID 1261764 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[O:13])=[CH:6][CH:5]=1.[H][H]>CO.[Pt](=O)=O>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)=[O:13])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 86672052HCID 86672052, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70816758HCID 70816758, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-{(E)-3-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-3-oxo-propenyl}-benzoic acid methyl ester (287 mg, 731 μmol) in methanol (12.2 mL) at 25° C. was treated with platinum (IV) oxide (8.3 mg, 36.5 μmol). The reaction was stirred under a balloon of hydrogen gas at 25° C. for 18 h. At this time, the reaction was filtered through a pad of Celite® to remove the catalyst. The Celite® was rinsed with a 10% solution of methanol/methylene chloride (2×30 mL). The filtrate was concentrated in vacuo to afford 4-{3-[4-chloro-2-(pyridin-2-ylamino)-phenyl]-3-oxo-propyl}-benzoic acid methyl ester (291 mg, quant.) as a dark green solid. The material was used without further purification.

Workup

  1. filtrationAt this time, the reaction was filtered through a pad of Celite®
  2. customto remove the catalyst
  3. washThe Celite® was rinsed with a 10% solution of methanol/methylene chloride (2×30 mL)
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bdbbf4837cc94c96a4085230ca2fb929
Source dataset
uspto-grants-2013_06
Patent number
US08471027B2

Reaction notes

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