Cesium fluoride → 1,7-Difluoro-4-cyclopropoxyisoquinoline

HRID 1852220Notes

Reaction equation

HRID 1852220 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13][CH:14]2[CH2:16][CH2:15]2)=[CH:4][N:3]=1.[F-:17].[Cs+]>CS(C)=O.O>[F:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([F:12])[CH:10]=2)[C:5]([O:13][CH:14]2[CH2:16][CH2:15]2)=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 717427171-Chloro-4-cyclopropoxy-7-fluoroisoquinoline

Product 1

HCID 709787051,7-Difluoro-4-cyclopropoxyisoquinolineYield 67.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
145 °C

Procedure

To a solution of 1-chloro-7-fluoro-4-cyclopropoxyisoquinolin (0.24 g, 1.01 mmol) in DMSO (2 ml) was added cesium fluoride (0.38 g 2.52 mmol) at room temperature. The reaction vessel (Pressure tube) was sealed and heated at 145° C. for 18 h. The reaction mass was diluted with water and extracted with ethyl acetate. The combined organic layer was dried over anhydrous Na2SO4 and evaporated under reduced pressure to get crude compound. The crude compound was purified by silica gel chromatography to get desired compound (0.15 g 67%) as a white solid.

Workup

  1. customThe reaction vessel (Pressure tube) was sealed
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  4. customevaporated under reduced pressure
  5. customto get crude compound
  6. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8cbde2c91c434bc59fdd166f2176efbb
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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