Potassium Carbonate → HCID 57861236, compound

HRID 1960044Notes

Reaction equation

HRID 1960044 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.[CH2:16]([O:23][CH2:24][CH2:25][C@H:26]1[CH2:31][CH2:30][C@H:29]([C@H:32]2[CH2:36][CH2:35][CH2:34][NH:33]2)[CH2:28][CH2:27]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.O.Cl.C(OCC)(=O)C>[CH2:16]([O:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][CH:29]([C@H:32]2[CH2:36][CH2:35][CH2:34][N:33]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)[CH2:28][CH2:27]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 218919362-Chloro-6,7-difluoroquinoline-3-carbaldehydeHCID 178420423HCID 178420423, compound

Product 1

HCID 57861236HCID 57861236, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2-chloro-6,7-difluoroquinoline-3-carbaldehyde (8.30 g, 36 mmol), trans-(R)-2-[4-(benzyloxyethyl)cyclohexyl]pyrrolidine (10.5 g, 36 mmol), and potassium carbonate (7.60 g, 55 mmol) in toluene (90 mL) and water (12 mL) is stirred and refluxed for 4 hours. The reaction mixture is cooled to room temperature and then diluted with 1N HCl aq. and ethyl acetate. The organic layer is washed with sat. NaHCO3 aq., brine, dried over magnesium sulfate, filtered and concentrated to give 2-((R)-2-{4-[2-(benzyloxy)ethyl]cyclohexyl}pyrrolidin-1-yl)-6,7-difluoroquinoline-3-carbaldehyde as yellow syrup, which is used without further purification.

Workup

  1. temperaturerefluxed for 4 hours
  2. washThe organic layer is washed with sat. NaHCO3 aq., brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-694c2cfe712643deaa8f3ac97974cac6
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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