Ethyl Acetate → Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

HRID 504283Notes

Reaction equation

HRID 504283 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].Cl[C:8]1[N:13]=[CH:12][C:11]([C:14]2([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)(=O)C>O.C1(C)C=CC=CC=1.C(O)C.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>[C:22]1([C:8]2[N:13]=[CH:12][C:11]([C:14]3([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:16][CH2:15]3)=[CH:10][CH:9]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86602273Ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate

Product 1

HCID 66661635Ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Sodium carbonate (42.4 mg, 0.400 mmol) in water (0.20 mL) was added to a mixture of ethyl 1-(6-chloropyridin-3-yl)cyclopropanecarboxylate (45.1 mg, 0.200 mmol), Phenylboronic acid (24.4 mg, 0.200 mmol) and tetrakis(triphenylphosphine)palladium(0) (7.15 mg) in toluene (200.0 μL) and ethanol (100.0 μL). The resulting mixture was irradiated by microwave at 120° C. for 15 minutes. Ethyl acetate (5 mL) was then added to the mixture. The resulting mixture was washed with water followed by brine. The organic layer was dried over Na2SO4, then filtered, and then concentrated under reduced pressure. The residue was purified by flash chromatography with ethyl acetate/hexane to give ethyl 1-(6-phenylpyridin-3-yl)cyclopropanecarboxylate.

Workup

  1. customThe resulting mixture was irradiated by microwave at 120° C. for 15 minutes
  2. washThe resulting mixture was washed with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography with ethyl acetate/hexane

Sources & evidence

ORD record
ord-8c4099067d9346ddb7e65023297c1a26
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

Loading…