Cesium fluoride → HCID 70978278, compound

HRID 1852141Notes

Reaction equation

HRID 1852141 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][O:16][CH3:17])[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][CH2:15][O:16][CH3:17])[N:3]=[C:2]2[F:18]

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 86683214HCID 86683214, compound

Product 1

HCID 70978278HCID 70978278, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1,5-dichloro-3-(2-methoxyethoxy)isoquinoline (578 mg, 2.124 mmol) in DMSO (5 mL) was added CsF (323 mg, 2.124 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 product purified via biotage (90 g column, 5-50% EtAOc:Hex) to give the product 5-chloro-1-fluoro-3-(2-methoxyethoxy)isoquinoline (250 mg, 46% yield) as a light yellow solid. MS: MS m/z 256.15(M++1).

Sources & evidence

ORD record
ord-5c0dabd8a5184fc6b2b834e37d0b2cfa
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…