Cesium fluoride → HCID 71742701, compound

HRID 1852115Notes

Reaction equation

HRID 1852115 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([F:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[F-:15].[Cs+]>CS(C)=O.CCOC(C)=O>[F:15][C:2]1[C:11]2[C:6](=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([F:12])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 717427031-Chloro-7-fluoro-5-methoxyisoquinoline

Product 1

HCID 71742701HCID 71742701, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-7-fluoro-5-methoxyisoquinoline (350 mg, 1.654 mmol) in DMSO (3 mL), was added CsF (502 mg, 3.31 mmol) and the mixture was heated to 140° C. for 4 h. The reaction was diluted with EtOAc and washed with water, and brine. The organic phase was collected, dried over sodium sulfate, and concentrated under vacuum to give 1,7-difluoro-5-methoxyisoquinoline (340 mg, 105% yield) which was not purified further. MS m/z 196.1 (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

Sources & evidence

ORD record
ord-c10dbc402c364ccd93f8463e129ce2f9
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…