Water → HCID 70664998, compound

HRID 1403619Notes

Reaction equation

HRID 1403619 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]([N:18]3[CH2:23][CH2:22][C:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)=[CH:20][CH2:19]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:30]([O:32][CH3:33])=[O:31])[CH:14]=3)[N:9]=2)=[CH:4][CH:3]=1.O>C(OCC)(=O)C.O=[Pt]=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:17]([N:18]3[CH2:19][CH2:20][CH:21]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=4)[CH2:22][CH2:23]3)=[N:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:30]([O:32][CH3:33])=[O:31])[CH:14]=3)[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 962WaterHCID 70664906HCID 70664906, compound

Product 1

HCID 70664998HCID 70664998, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 2-(4-fluorophenyl)-3-(4-(pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)quinoxaline-6-carboxylate (150 mg, 0.34 mmol) in ethyl acetate (30 ml) was added PtO2 (38 mg) and the reaction mixture was stirred at room temperature for 2 hours under an atmosphere of H2(g). The reaction mixture was added to water (100 ml), extracted with dichloromethane (3×30 mL), and the organic layers combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the residue, which was purified via silica gel column chromatography (2% ethyl acetate in petroleum ether) to afford methyl 2-(4-fluorophenyl)-3-[4-(pyridin-2-yl)piperidin-1-yl]quinoxaline-6-carboxylate as a yellow solid (84 mg, 56%).

Workup

  1. extractionextracted with dichloromethane (3×30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the residue, which
  5. customwas purified via silica gel column chromatography (2% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-eeab48c94664439d97b60efad7148718
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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