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Cesium carbonate → (S)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline

HRID 339086
Notes
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Reaction equation

HRID 339086 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.C([O-])([O-])=O.[Cs+].[Cs+].CC1C=CC(S(O[CH2:31][C@@H:32]([O:34][CH3:35])[CH3:33])(=O)=O)=CC=1>CN1C(=O)CCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:31][C@@H:32]([O:34][CH3:35])[CH3:33])[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 13896528(2S)-2-methoxypropyl 4-methylbenzene-1-sulfonateHCID 1363380756-Fluoro-2-methylquinolin-7-ol

Product 1

HCID 70983212(S)-6-fluoro-7-(2-methoxypropoxy)-2-methylquinoline

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred mixture of 6-fluoro-2-methylquinolin-7-ol (0.200 g, 1.13 mmol), Cs2CO3 (0.552 g, 1.69 mmol) and NMP (2.3 mL) was added (S)-2-methoxypropyl 4-methylbenzenesulfonate (0.303 g, 1.24 mmol). The reaction mixture was heated at 80° C. for 1 hour. After cooling, the reaction was partitioned between toluene and water. The aqueous layer was extracted with toluene. The combined organic layers were washed with water and brine, dried and concentrated to give the crude product, which was used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. customthe reaction was partitioned between toluene and water
  3. extractionThe aqueous layer was extracted with toluene
  4. washThe combined organic layers were washed with water and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-43305870496140d0a8b4005e89522c15
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes