Potassium Carbonate → HCID 67293036, compound

HRID 1685409Notes

Reaction equation

HRID 1685409 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][C:5]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=1.[C:17]1(B(O)O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Li+].C(=O)([O-])[O-].[K+].[K+]>O.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.COCCOC>[C:17]1([C:2]2[C:7]([F:8])=[CH:6][C:5]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:4][N:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 433294Lithium ChlorideHCID 86625023HCID 86625023, compound

Product 1

HCID 67293036HCID 67293036, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

6.8 g (28.6 mM) of 2-chloro-3-fluoro-5-(phenylmethoxy)pyridine, 110 ml of DME and 4.18 g (34 mM) of phenylboronic acid are mixed. 6.64 g (156 mM) of lithium chloride and 1.65 g (1.4 mM) of tetrakis(triphenylphosphine)palladium are added. Finally, 38 ml (76 mM) of 2 M potassium carbonate solution are added and the mixture is refluxed for 18 hours. After hydrolysis in 250 ml of water, the mixture is extracted with ethyl acetate and the organic phases are washed with water and then with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (95/5, then 90/10; v/v) as the eluent to give the desired product in the form of a white solid with a yield of 84%.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washthe organic phases are washed with water
  4. dry with materialwith brine, dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel using a cyclohexane/ethyl acetate mixture (95/5

Sources & evidence

ORD record
ord-c937f9c61dfd490b9acd8f794f8864da
Source dataset
uspto-grants-2012_04
Patent number
US08148407B2

Reaction notes

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