Toluene → HCID 57861256, compound

HRID 1518077Notes

Reaction equation

HRID 1518077 reaction equation
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:15])=[C:7]([F:14])[CH:8]=2)[N:3]=1.[C:16](=[O:19])([O-])[O-].[K+].[K+].[C:22]1([CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O.C(OCC)(=O)C>[CH2:28]([O:19][CH2:16][CH:25]1[CH2:26][CH2:27][CH:22]([C@H:28]2[CH2:10][CH2:11][CH2:2][N:3]2[C:2]2[C:11]([CH:12]=[O:13])=[CH:10][C:9]3[C:4](=[CH:5][C:6]([F:15])=[C:7]([F:14])[CH:8]=3)[N:3]=2)[CH2:23][CH2:24]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 218919362-Chloro-6,7-difluoroquinoline-3-carbaldehyde

Product 1

HCID 57861256HCID 57861256, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-chloro-6,7-difluoroquinoline-3-carbaldehyde (4.97 g, 18 mmol), trans-(R)-2-[(4-benzyloxymethyl)cyclohexyl]pyrrolidine (5.39 g, 20 mmol) and potassium carbonate (2.97 g, 21 mol) in toluene (100 mL) and water (10 mL) is stirred and refluxed for 3 hours. The reaction mixture is cooled to room temperature and then diluted with water and ethyl acetate. The organic layer is washed with water, citric acid aq., brine, dried over magnesium sulfate, filtered and concentrated. The crude product is purified by silica gel column chromatography to give 2-{(R)-2-[4-(benzyloxymethyl)cyclohexyl]pyrrolidin-1-yl}-6,7-difluoroquinoline-3-carbaldehyde as a yellow syrup.

Workup

  1. temperaturerefluxed for 3 hours
  2. washThe organic layer is washed with water, citric acid aq., brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a4f27eca583649a3955a8d68ee691220
Source dataset
uspto-grants-2012_07
Patent number
US08232403B2

Reaction notes

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