Cesium fluoride → HCID 71005172, compound

HRID 1852135Notes

Reaction equation

HRID 1852135 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][CH2:14][CH2:15][CH3:16])[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][CH2:14][CH2:15][CH3:16])[N:3]=[C:2]2[F:17]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683210HCID 86683210, compound

Product 1

HCID 71005172HCID 71005172, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1,5-dichloro-3-propoxyisoquinoline (565 mg, 2.206 mmol) in DMSO (5 mL) was added CsF (369 mg, 2.427 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. Crude material purified via silica gel chromatography (90 g column; 0-40% EtOAc:Hex) to get the product 5-chloro-1-fluoro-3-propoxyisoquinoline (440 mg, 83% yield) as a yellow solid. MS: MS m/z 240.05(M++1).

Sources & evidence

ORD record
ord-9b7e9eed658f46b4a76d9c97f88eef9f
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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