Cesium fluoride → HCID 70979172, compound

HRID 1852156Notes

Reaction equation

HRID 1852156 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:14][CH3:15])[N:3]=1.[F-:16].[Cs+]>CS(C)=O>[F:16][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([O:14][CH3:15])[N:3]=1

Participants

4

Reactant 2

HCID 25953Cesium fluorideHCID 25243049HCID 25243049, compound

Product 1

HCID 70979172HCID 70979172, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-3,6-dimethoxyisoquinoline (300 mg, 1.341 mmol) in DMSO (5 mL) was added CsF (408 mg, 2.68 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 1-fluoro-3,6-dimethoxyisoquinoline (250 mg, 90% yield) as a reddish brown solid. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.93 (d, J=9.0 Hz, 1H), 7.03 (dd, J=9.3, 2.3 Hz, 1H), 6.95 (t, J=1.9 Hz, 1H), 6.75 (s, 1H), 4.01-3.96 (m, 3H), 3.96-3.90 (m, 3H). MS: MS m/z 208.07(M++1).

Sources & evidence

ORD record
ord-d43c9bb7cd7f471e8bf0e859d073aa0a
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

Loading…