Potassium Carbonate → HCID 86683032, compound

HRID 1497210Notes

Reaction equation

HRID 1497210 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].[C:12]([O:16][C:17]([C:19]1[C:20](OS(C(F)(F)F)(=O)=O)=[N:21][C:22]2[C:27]([C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[CH:26][C:25]([Cl:36])=[CH:24][CH:23]=2)=[O:18])([CH3:15])([CH3:14])[CH3:13]>CS(C)=O.O>[C:12]([O:16][C:17]([C:19]1[C:20]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:21][C:22]2[C:27]([C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)=[CH:26][C:25]([Cl:36])=[CH:24][CH:23]=2)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 86683033HCID 86683033, compound

Product 1

HCID 86683032HCID 86683032, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of pyrrolidine (0.047 ml, 0.58 mmol) in DMSO (5 ml) was added K2CO3 (159 mg, 1.15 mmol) and 6-chloro-4-(3-chloro-phenyl)-2-trifluoromethanesulfonyloxy-quinoline-3-carboxylic acid tert-butyl ester (prepared as described in example 91 step C, 150 mg, 0.29 mmol) at room temperature. The resulting reaction mixture was stirred at 90° C. for 3 h. After cooling, the reaction mixture was diluted with water (15 ml) and extracted with ethyl acetate (3×30 ml). The separated organic layer was washed with brine (15 ml), dried over sodium sulfate and concentrated under vacuum to give a crude residue which was purified by column chromatography eluting with 5-10% ethyl acetate in hexane to yield 6-chloro-4-(3-chloro-phenyl)-2-pyrrolidin-1-yl-quinoline-3-carboxylic acid tert-butyl ester (90 mg, 71% yield) as a pale yellow solid. LC-MS (ESI): 443 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. washThe separated organic layer was washed with brine (15 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customto give a crude residue which
  8. customwas purified by column chromatography
  9. washeluting with 5-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8c269c2814d4445dac87f617cda3a977
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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