Ethylene Glycol → HCID 118113230, compound

HRID 1485054Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([CH:8]2[CH2:10][CH2:9]2)=[CH:6][CH:7]=1.[CH:11]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)=[O:12].P([O-])([O-])([O-])=O.[K+].[K+].[K+].C(O)CO>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.O>[CH:8]1([C:5]2[N:4]=[CH:3][C:2]([C:16]3[CH:17]=[CH:18][C:13]([CH:11]=[O:12])=[CH:14][CH:15]=3)=[CH:7][CH:6]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-bromo-6-(cyclopropyl)pyridine (2.00 g), 4-formylphenylboronic acid (1.82 g), palladium(II) acetate (113 mg), tripotassium phosphate (4.50 g) and ethylene glycol (16.8 mL) was stirred at 80° C. for 3 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter the crude product was adsorbed on diatomaceous earth, with the solvent being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-50:50) to give the titled compound as a colorless solid (1.81 g).

Workup

temperatureAfter cooling the reaction mixture to room temperature
washThe combined organic layers were washed with saturated brine
distillationbeing distilled off under reduced pressure
customwas purified by silica gel column chromatography (hexane:ethyl acetate=98:2-50:50)

Sources & evidence

ORD record: ord-1d0a9e034b254d8c8bf85c13da673d8e
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422240B2

Reaction notes

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