Potassium Carbonate → HCID 86683009, compound

HRID 1497175Notes

Reaction equation

HRID 1497175 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6]([O:10][C:11]([C:13]1[C:14](OS(C(F)(F)F)(=O)=O)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([CH3:31])[CH3:30])[CH:24]=1)=[CH:20][C:19]([Cl:32])=[CH:18][CH:17]=2)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[C:6]([O:10][C:11]([C:13]1[C:14]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:15][C:16]2[C:21]([C:22]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([CH3:30])[CH3:31])[CH:24]=1)=[CH:20][C:19]([Cl:32])=[CH:18][CH:17]=2)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 86683008HCID 86683008, compound

Product 1

HCID 86683009HCID 86683009, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of pyrrolidine (0.093 ml, 1.13 mmol) in DMSO (7 ml) was added 6-chloro-4-(3-isopropyl-phenyl)-2-trifluoromethanesulfonyloxy-quinoline-3-carboxylic acid tert-butyl ester (prepared as described in example 78 step C, 400 mg, 0.76 mmol) and potassium carbonate (313 mg, 2.026 mmol) at 25° C. The resulting reaction mixture was stirred at 90° C. for 3 h. The reaction mixture was diluted with water (15 ml), and extracted with EtOAc (2×30 ml). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (5-10% EtOAc in hexane) to afford 6-chloro-4-(3-isopropyl-phenyl)-2-pyrrolidin-1-yl-quinoline-3-carboxylic acid tert-butyl ester (250 mg, 73%) as pale yellow solid. LC-MS (ESI): LC-MS (ESI): 451 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (2×30 ml)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude residue which
  7. customwas purified by flash column chromatography (5-10% EtOAc in hexane)

Sources & evidence

ORD record
ord-ab61d5aaebe641a688d03825e180a2be
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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