Potassium Carbonate → Ethyl 5-bromo-2-(2-nitropyridin-3-yl)-3-oxo-2,3-dihydro-1-benzofuran-2-carboxylate

HRID 931376Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7](=[O:15])[C:6]=2[CH:16]=1.[N+:17]([C:20]1[C:25](F)=[CH:24][CH:23]=[CH:22][N:21]=1)([O-:19])=[O:18].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:25]3[C:20]([N+:17]([O-:19])=[O:18])=[N:21][CH:22]=[CH:23][CH:24]=3)([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:7](=[O:15])[C:6]=2[CH:16]=1

Participants

Conditions

Temperature: 87.5 °C

Procedure

A mixture of ethyl 5-bromo-3-oxo-2,3-dihydro-1-benzofuran-2-carboxylate (1.42 g, 5.0 mmol), 2-nitro-3-fluoropyridine (0.71 g, 5 mmol) and potassium carbonate (0.83 g, 6.0 mmol) in DMSO (15 mL) is heated at 85-90° C. for 18 h. The mixture is cooled to ambient temperature and partitioned between EtOAc and brine. The layers are separated and the aqueous layer is further extracted with EtOAc. The combined organic extracts are dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc) to afford the title compound.

Workup

temperatureThe mixture is cooled to ambient temperature
custompartitioned between EtOAc and brine
customThe layers are separated
extractionthe aqueous layer is further extracted with EtOAc
dry with materialThe combined organic extracts are dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is purified by silica gel chromatography (gradient elution with hexanes-EtOAc)

Sources & evidence

ORD record: ord-3e8ea1c00e014b29a6944455a9b9c773
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296750B2

Reaction notes

Loading…