Cesium fluoride → HCID 70978421, compound

HRID 1852067Notes

Reaction equation

HRID 1852067 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][CH2:14][CH3:15])=[CH:4][N:3]=1.[F-:16].[Cs+]>CS(C)=O.C(OC(=O)C)C>[F:16][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH3:15])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 57590857HCID 57590857, compound

Product 1

HCID 70978421HCID 70978421, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-4-propoxyisoquinoline (1.1 g, 4.96 mmol) in DMSO (6 mL), added CsF (1.508 g, 9.92 mmol) and heated to 140° C. for 6 h. 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 5-25% EtOAc/Hexanes. The product fractions were collected and the solvent removed under vacuum to give 700 mg of the desired product 1-fluoro-4-propoxyisoquinoline as a white solid. MS: MS m/z 206.17 (M++1).

Workup

  1. washwashed with water, and brine
  2. customThe organic phase was collected
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product which
  6. customwas purified by silica gel chromatography
  7. customThe product fractions were collected
  8. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-ee32ca473df94f58ac98e900619bcd76
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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