Cesium fluoride → HCID 70979074, compound

HRID 1852139Notes

Reaction equation

HRID 1852139 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:13][CH:14]([CH3:16])[CH3:15])[N:3]=1.[F-:17].[Cs+]>CS(C)=O>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[C:4]([O:13][CH:14]([CH3:16])[CH3:15])[N:3]=[C:2]2[F:17]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683213HCID 86683213, compound

Product 1

HCID 70979074HCID 70979074, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1,5-dichloro-3-isopropoxyisoquinoline (598 mg, 2.335 mmol) in DMSO (5 mL) was added CsF (390 mg, 2.57 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. Crude material purified via silica gel chromatography (90 g column; 0-40% EtOAc:Hex) to get the product 5-chloro-1-fluoro-3-isopropoxyisoquinoline (520 mg, 93% yield) as a yellow solid. MS: MS m/z 240.15(M++1).

Sources & evidence

ORD record
ord-581446f7e2da43a8b3725b929defd132
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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