Cesium fluoride → HCID 86683216, compound

HRID 1852143Notes

Reaction equation

HRID 1852143 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH2:15][CH:16]([F:18])[F:17])=[CH:4][N:3]=1.[F-:19].[Cs+]>CS(C)=O>[F:17][CH:16]([F:18])[CH2:15][O:14][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=2)[C:2]([F:19])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 866832151-Chloro-4-(2,2-difluoroethoxy)-6-methoxyisoquinoline

Product 1

HCID 86683216HCID 86683216, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-4-(2,2-difluoroethoxy)-6-methoxyisoquinoline (538 mg, 1.966 mmol) in DMSO (5 mL) was added CsF (597 mg, 3.93 mmol) and heated to 140° C. for 2 hrs. LC/MS showed the desired product. The reaction was diluted with ethyl acteate and washed with water, and brine. The organic phase was collected, dried over MgSO4, and concentrated under vacuum to give the crude product as a reddish brown solid. The crude material was purified via silica gel chromatography (5-50% EtOAc:Hex) to give the product 4-(2,2-difluoroethoxy)-1-fluoro-6-methoxyisoquinoline (237 mg, 0.921 mmol, 46.9% yield) as a light yellow solid. MS: MS m/z 258.2(M++1).

Sources & evidence

ORD record
ord-e89a1b6fdeb94947a4b261801c536c43
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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