Potassium Phosphate, Tribasic → tert-Butyl 2-(5-(2-methylpyridin-4-yl)-3-nitropyridin-2-yloxy)acetate

HRID 1628322Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N:6][CH:7]=1.[CH3:20][C:21]1[CH:26]=[C:25](B(O)O)[CH:24]=[CH:23][N:22]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([N+:17]([O-:19])=[O:18])[C:5]([O:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N:6][CH:7]=2)[CH:24]=[CH:23][N:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a flask with tert-butyl 2-(5-bromo-3-nitropyridin-2-yloxy)acetate (78.F) (700 mg from last step, about 406 mg of estimated pure 78.F by NMR) was added tris(dibenzylideneacetone)dipalladium (o) (67 mg, 0.073 mmol), 2-methylpyridin-4-ylboronic acid (250 mg, 1.8 mmol), X-phos (139 mg, 0.29 mmol), potassium phosphate (1.04 g, 4.9 mmol). The solids were purged with nitrogen. Degassed t-amyl alcohol was added as a solvent. The reaction was heated at 100° C. for 2 hr. 40 min.s. The solids were filtered off. Silica gel purification afforded 280 mg (67%) 78.G.

Workup

customThe solids were purged with nitrogen
additionDegassed t-amyl alcohol was added as a solvent
custom40 min
filtrationThe solids were filtered off
customSilica gel purification

Sources & evidence

ORD record: ord-7269e9f0f0a441d3bdd5cdbd06cdd19e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785468B2

Reaction notes

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