Cesium fluoride → HCID 71742704, compound

HRID 1852116Notes

Reaction equation

HRID 1852116 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F-:15].[Cs+]>CS(C)=O.C(OC(=O)C)C>[F:15][C:2]1[C:11]2[C:6](=[C:7]([F:14])[C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 222501071-Chloro-5-fluoro-6-methoxyisoquinoline

Product 1

HCID 71742704HCID 71742704, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-5-fluoro-6-methoxyisoquinoline (0.5 g, 2.363 mmol) in DMSO (5 mL), was added CsF (0.718 g, 4.73 mmol). The mixture was heated to 140° C. for 2 h. The reaction was diluted with ethylacteate and washed with water, and brine. The organic phase was collected, dried over sodium sulfate, and concentrated under vacuum to give the crude product which was purified by silica gel chromatography using a gradient of 30-50% DCM in hexanes. The product fractions were collected and the solvent was removed under vacuum to give 1,5-difluoro-6-methoxyisoquinoline (340 mg, 74% yield). MS m/z 196.2 (M++1).

Workup

  1. washwashed with water, and brine
  2. customThe organic phase was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product which
  6. customwas purified by silica gel chromatography
  7. customThe product fractions were collected
  8. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-10e3dae2dbb842758fd823c8f6f41f99
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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