Water → HCID 59631169, compound

HRID 1431724Notes

Reaction equation

HRID 1431724 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:15]=[N:16][C:17](F)=[CH:18][CH:19]=2)[C:3]=1[CH3:21].[NH:22]1[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([N:22]3[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23]3)=[N:16][CH:15]=2)[C:3]=1[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 982104-HydroxypyrrolidineHCID 59631044HCID 59631044, compound

Product 1

HCID 59631169HCID 59631169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of 4-chloro-5,7-difluoro-2-(6-fluoropyridin-3-yl)-3-methylquinoline (0.1 g, 0.32 mmol) in DMF (2.5 mL) was added 3-pyrrolidinol (0.029 mL, 0.36 mmol) followed by potassium carbonate (0.090 g, 0.65 mmol). The reaction was stirred at 120° C. and stirring continued for 1.6 h. After which, the reaction mixture was cooled to rt and water was added. The crude reaction mixture was extracted with EtOAc, dried over magnesium sulfate and concd in vacuo. The crude material was purified on silica gel, eluting with 0-30% EtOAc in hexanes to provide 1-(5-(4-chloro-5,7-difluoro-3-methylquinolin-2-yl)pyridin-2-yl)pyrrolidin-3-ol as a yellow solid. Mass Spectrum (ESI) m/e=376.1 (M+1).

Workup

  1. stirringstirring
  2. temperatureAfter which, the reaction mixture was cooled to rt
  3. customThe crude reaction mixture
  4. extractionwas extracted with EtOAc
  5. dry with materialdried over magnesium sulfate and concd in vacuo
  6. customThe crude material was purified on silica gel
  7. washeluting with 0-30% EtOAc in hexanes

Sources & evidence

ORD record
ord-003cca69f8154ba0a982f88f9710509a
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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