Cesium fluoride → HCID 22504971, compound

HRID 1813968Notes

Reaction equation

HRID 1813968 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[CH:13][C:14]([O:20][CH3:21])=[C:15](B(O)O)[CH:16]=1.[F-].[Cs+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([C:13]2[CH:12]=[C:11]([Cl:10])[CH:16]=[CH:15][C:14]=2[O:20][CH3:21])[N:3]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27665Pyridine, 2,4,6-trichloro-HCID 27357515-Chloro-2-methoxyphenylboronic acid

Product 1

HCID 22504971HCID 22504971, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2,4,6-trichloropyridine (50 mg, 0.27 mmol), 5-chloro-2-methoxy-phenylboronic acid (54 mg, 0.28 mmol), cesium fluoride (100 mg, 0.66 mmol) in ethylene glycol dimethyl ether (10 ml), degassed with argon, was added tetrakis(triphenylphosphine)palladium(0) (30 mg, 0.026 mmol). The mixture was heated under reflux for 2 hours and filtered through a pad of celite under suction. The filtrate was concentrated under reduced pressure. The residue was purified by preparative thin layer chromatography eluting with ethyl acetate-hexane (1:9) to provide 2,4-dichloro-6-(5-chloro-2-methoxy-phenyl)-pyridine (25 mg, 32% yield). 1H NMR (acetone-d6) δ 3.95 (s, 3H, CH3), 7.24 (d, 1H, J=8.9 Hz, Ar), 7.49 (dd, 1H, J=8.9 Hz, J=2.8 Hz, Ar), 7.56 (d, 1H, J=2.8 Hz, Ar), 7.94 (d, 1H, J=2.8 Hz, Ar), 8.10 (d, 1H, J=1.6 Hz, Ar).

Workup

  1. customdegassed with argon
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. filtrationfiltered through a pad of celite under suction
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography
  7. washeluting with ethyl acetate-hexane (1:9)

Sources & evidence

ORD record
ord-9e8bcad3a00b4ed6aa91b5b14ebbb21e
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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