Potassium Carbonate → HCID 70494851, compound

HRID 2408116Notes

Reaction equation

HRID 2408116 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Cl:24])[CH:8]=[C:9]2[C:14]=1[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)[CH2:11][C:10]2([CH3:23])[CH3:22])=[O:4].[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I.C(OCC)(=O)C>[Cl:24][C:7]1[CH:8]=[C:9]2[C:14](=[C:5]([C:3]([OH:2])=[O:4])[CH:6]=1)[NH:13][CH:12]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:16]=1)[CH2:11][C:10]2([CH3:22])[CH3:23]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 67291316HCID 67291316, compound

Product 1

HCID 70494851HCID 70494851, compoundYield 40.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-(3-bromo-phenyl)-6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid methyl ester (0.82 g, 2.0 mmol), pyrrolidine (0.28 g, 4 mmol), copper (I) iodide (230 mg, 1.2 mmol), N,N-dimethyl glycine hydrochloride (220 mg, 1.6 mmol) and potassium carbonate (0.83 g, 6 mmol) in dimethylsulfoxide (20 mL) was heated for 12 h at 120° C. After colling to room temperature, the mixture was treated with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes) to afford 6-chloro-4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (0.31 g, 40%) as a white solid: MS (ESI) M+1=385.2.

Workup

  1. customAfter colling to room temperature
  2. washwashed with water (20 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-57b536296139446eb3f51ee64f8d19a6
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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