Cesium fluoride → HCID 70979030, compound

HRID 1852145Notes

Reaction equation

HRID 1852145 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][CH2:16][O:17][CH3:18])=[CH:4][N:3]=1.[F-:19].[Cs+]>CS(C)=O>[F:19][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][CH2:16][O:17][CH3:18])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683217HCID 86683217, compound

Product 1

HCID 70979030HCID 70979030, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-6-methoxy-4-(2-methoxyethoxy)isoquinoline (560 mg, 2.092 mmol) in DMSO (5 mL) was added CsF (636 mg, 4.18 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 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 1-fluoro-6-methoxy-4-(2-methoxyethoxy)isoquinoline (168 mg, 0.669 mmol, 32.0% yield) as a light yellow solid. MS: MS m/z 252.2(M++1).

Sources & evidence

ORD record
ord-082647355cdb473eb94eadf48793f308
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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