HCID 58368424, compound → HCID 58368595, compound

HRID 1192567Notes

Reaction equation

HRID 1192567 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:20](=[O:22])[CH3:21])=[CH:10][C:11]([CH:18]=[CH2:19])=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:5]=[CH:6][CH:7]=1.[H][H]>[Pd].CO>[CH2:18]([C:11]1[CH:10]=[C:9]([C:20](=[O:22])[CH3:21])[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[C:17]2[C:12]=1[CH:13]=[CH:14][CH:15]=[N:16]2)[CH3:19]

Participants

5

Reactant 2

HCID 58368424HCID 58368424, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58368595HCID 58368595, compoundYield 20.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[8-(3-fluorophenyl)-5-vinylquinolin-7-yl]ethanone (0.03 g, 0.1 mmol) and 5% palladium on carbon (3 mg) in methanol (1 mL) was treated with hydrogen under balloon pressure, at room temperature, for 3 hours. The mixture was filtered. The filtrate was concentrated and purified on silica gel (eluting with 0 to 10% Ethyl acetate in hexane) to give the desired product (6.1 mg, 20%). LCMS calculated for C19H17FNO (M+H)+: m/z=294.1; Found: 294.1.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationThe filtrate was concentrated
  3. custompurified on silica gel (eluting with 0 to 10% Ethyl acetate in hexane)

Sources & evidence

ORD record
ord-60952a7c47af4548b0c0cc7a07e7b149
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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