Cesium fluoride → HCID 86683206, compound

HRID 1852131Notes

Reaction equation

HRID 1852131 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][CH:14]([F:16])[F:15])=[CH:4][N:3]=1.[F-:17].[Cs+]>CS(C)=O>[F:15][CH:14]([F:16])[CH2:13][O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([F:17])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683207HCID 86683207, compound

Product 1

HCID 86683206HCID 86683206, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-4-(2,2-difluoroethoxy)isoquinoline (630 mg, 2.59 mmol) in DMSO (10 mL) was added CsF (786 mg, 5.17 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 5-50% EtOAc/Hexanes. The product fractions were collected and the solvent removed under vacuum to give it the desired product 4-(2,2-difluoroethoxy)-1-fluoroisoquinoline (310 mg, 52.8% yield). MS: MS m/z 228.1 (M++1).

Sources & evidence

ORD record
ord-714a85221bb245e98bb94b42417d81b2
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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