Water → HCID 57815340, compound

HRID 385548Notes

Reaction equation

HRID 385548 reaction equation
Cl[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][O:10][CH2:11][O:12][CH3:13])=[C:4]([Cl:14])[N:3]=1.O.C(OCC)(=O)C>CN(C)C=O.C(N(CC)CC)C.C(O)=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>[Cl:14][C:4]1[C:5]([CH2:9][O:10][CH2:11][O:12][CH3:13])=[CH:6][C:7]([F:8])=[CH:2][N:3]=1

Participants

8

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57815444HCID 57815444, compound

Product 1

HCID 57815340HCID 57815340, compoundYield 73.4%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 284Formic AcidSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 0.62 g of 2,6-dichloro-3-fluoro-5-((methoxymethoxy)methyl)pyridine in 18 mL of N,N-dimethylformamide, 0.54 mL of triethylamine, 0.15 mL of formic acid and 0.15 g of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was stirred at 90 to 100° C. for 4 hours 30 minutes under a nitrogen atmosphere. Thereto were added water and ethyl acetate, the insoluble substance was filtered off, the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed sequentially with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of hexane:ethyl acetate=8:1 to obtain 0.39 g of 2-chloro-5-fluoro-3-((methoxymethoxy)methyl)pyridine as a colorless oily substance.

Workup

  1. filtrationthe insoluble substance was filtered off
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe resultant solution was washed sequentially with water
  5. dry with materiala saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-33fb8ce6bd7d4cc8bf8ed2143b6bf848
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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