Cesium fluoride → HCID 86683212, compound

HRID 1852137Notes

Reaction equation

HRID 1852137 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][CH:15]([F:17])[F:16])[N:3]=1.[F-:18].[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][CH:15]([F:17])[F:16])[N:3]=[C:2]2[F:18]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683211HCID 86683211, compound

Product 1

HCID 86683212HCID 86683212, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1,5-dichloro-3-(2,2-difluoroethoxy)isoquinoline (581 mg, 2.089 mmol) in DMSO (5 mL) was added CsF (349 mg, 2.298 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-3-(2,2-difluoroethoxy)-1-fluoroisoquinoline (450 mg, 82% yield) as a yellow solid. MS: MS m/z 262.1(M++1).

Sources & evidence

ORD record
ord-0848cceed4f547649d2df0c36738ec6c
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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