Ethyl Acetate → HCID 58452481, compound

HRID 70541Notes

Reaction equation

HRID 70541 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5](I)=[CH:4][CH:3]=1.[CH:11]1(B(O)O)[CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH:11]2[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2760897Cyclopropylboronic acidHCID 582361006-bromo-3-iodo-2-methoxypyridine

Product 1

HCID 58452481HCID 58452481, compoundYield 107.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Palladium acetate (36 mg) was added to a suspension of 6-bromo-3-iodo-2-methoxypyridine (1.0 g), cyclopropylboronic acid (547 mg), triphenylphosphine (84 mg) and potassium carbonate (1.32 g) in toluene (20 mL) and water (1 mL), and the mixture was stirred at 110° C. for 4.5 hours. Water and ethyl acetate were added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1→96:4) to give the title compound as a colorless oil (782 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=99:1→96:4)

Sources & evidence

ORD record
ord-2e60ceeaae754ad39a9869257f0b01eb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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