Cesium fluoride → HCID 70978872, compound

HRID 1852062Notes

Reaction equation

HRID 1852062 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[C:4]([C:16]2[CH:21]=[CH:20][C:19](CC(C)C)=[CH:18][CH:17]=2)[N:3]=1.[F-:26].[Cs+]>CS(C)=O.C(OC(=O)C)C>[F:26][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([O:14][CH3:15])=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([O:12][CH:8]([CH3:9])[CH3:7])=[CH:18][CH:17]=2)[N:3]=1

Participants

5

Reactant 2

HCID 25953Cesium fluorideHCID 86683171HCID 86683171, compound

Product 1

HCID 70978872HCID 70978872, compoundYield 175.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 1-chloro-3-(4-isobutylphenyl)-4,6-dimethoxyisoquinoline (142 mg, 0.4 mmol) in DMSO (2 mL), was added CsF (122 mg, 0.800 mmol) and the mixture was heated to 140° C. for 4 hrs. 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 120 mg of the desired product as a white solid containing starting material. MS: MS m/z 342.1 (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-178d46990ec1413aa00fd849360fbbe2
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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