Potassium Phosphate, Tribasic → 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester

HRID 553763Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[CH:7]=[C:6]([N+:19]([O-:21])=[O:20])[CH:5]=1.Br[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COC=COC.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:5]=[C:6]([N+:19]([O-:21])=[O:20])[CH:7]=[C:8]([C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=2)[CH:9]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of 3-Nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (100 mg, 0.326 mmol), 2-bromo-5 methyl-pyridine (56 mg, 0.326 mmol), K3PO4 (138 mg, 0.652 mmol) in dimethoxy ethylene (3 mL) and water (1 mL) was added Pd(Pph3)4 (11.3 mg, 0.001 mmol). The mixture was flushed with N2 and heated under microwave at 130° C. for 30 minutes. The reaction mixture was cooled, solvent was removed under reduced pressure, and the residue was purified by column chromatography (EtOAc/hexane=1:3) to afford 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (50 mg, 56%). MS (M+H)=273.

Workup

customThe mixture was flushed with N2
temperatureThe reaction mixture was cooled
customsolvent was removed under reduced pressure
customthe residue was purified by column chromatography (EtOAc/hexane=1:3)

Sources & evidence

ORD record: ord-95ced75f2e7a429aa97eca3f92a05540
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048905B2

Reaction notes

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