Cesium fluoride → 1-Fluoro-4-(2-methoxyethoxy)isoquinoline

HRID 1852132Notes

Reaction equation

HRID 1852132 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:4][N:3]=1.[F-:17].[Cs+]>CS(C)=O>[F:17][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][O:15][CH3:16])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683208HCID 86683208, compound

Product 1

HCID 709782881-Fluoro-4-(2-methoxyethoxy)isoquinoline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-4-(2-methoxyethoxy)isoquinoline (368 mg, 1.548 mmol) in DMSO (7 mL) was added CsF (470 mg, 3.10 mmol) and heated to 140° C. for 2 hrs. LC/MS showed the desired product. 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 5-25% EtOAc/Hexanes. The product fractions were collected and the solvent removed under vacuum to give it the desired product 1-fluoro-4-(2-methoxyethoxy)isoquinoline (241 mg, 70.4% yield) as a white solid. MS: MS m/z 222.15 (M++1).

Sources & evidence

ORD record
ord-6ef9b9e6c4e94ae5a61251631762d6ee
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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