Potassium Carbonate → HCID 70496316, compound

HRID 2408071Notes

Reaction equation

HRID 2408071 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)[CH2:9][C:8]2([CH3:23])[CH3:22])=[O:4].[NH:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1.Cl.CN(C)CC(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:16]=1)[CH2:9][C:8]2([CH3:23])[CH3:22])=[O:4]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 75605N,N-Dimethylglycine hydrochlorideHCID 66587676HCID 66587676, compound

Product 1

HCID 70496316HCID 70496316, compoundYield 93.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture solution of 2-(3-bromo-phenyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.94 g, 5 mmol), pyrrolidine (2.1 mL, 25 mmol), copper(I) iodide (0.38 g, 2 mmol), N,N-dimethylglycine hydrochloride (0.42 g, 3 mmol), and potassium carbonate (2.07 g, 15 mmol) in dimethyl sulfoxide (10 mL) was stirred at 120° C. for 16 h. Then the reaction mixture was cooled to room temperature. The reaction mixture was extracted with ethyl acetate (50 mL×2), washed with saturated aqueous ammonium chloride solution (20 mL×3) and brine (20 mL×2), dried over anhydrous sodium sulfate and then concentrated in vacuo and the residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether) to afford 4,4-dimethyl-2-(3-pyrrolidin-1-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid methyl ester (1.7 g, 90%) as a yellow solid: MS (ESI) M+1=379.1.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (50 mL×2)
  2. washwashed with saturated aqueous ammonium chloride solution (20 mL×3) and brine (20 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by ISCO combi-flash chromatography (gradient elution, 30-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-4c5a1feb79e84072817bfb08432b7352
Source dataset
uspto-grants-2014_08
Patent number
US08809369B2

Reaction notes

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