Potassium Carbonate → HCID 59631253, compound

HRID 1431729Notes

Reaction equation

HRID 1431729 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].[CH3:22][N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[K+].[K+]>O>[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]([N:26]3[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]3)=[CH:18][CH:19]=2)[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 59631044HCID 59631044, compound

Product 1

HCID 59631253HCID 59631253, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 4-chloro-5,7-difluoro-2-(6-fluoropyridin-3-yl)-3-methylquinoline (0.1 g, 0.324 mmol) in dmf (0.025 mL, 0.32 mmol) was added 1-methylpiperazine (0.036 g, 0.356 mmol) followed by potassium carbonate (0.090 g, 0.65 mmol). The reaction was stirred at 80° C. and stirring continued for 19 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 4-chloro-5,7-difluoro-3-methyl-2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)quinoline as a white solid. Mass Spectrum (ESI) m/e=389.1 (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-eb3ae6c3f32c405ebe3a349e5f9d1aa3
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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