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

HRID 553763
Notes
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Reaction equation

HRID 553763 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 5642162-Bromo-5-methylpyridineHCID 44119765Methyl 3-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Product 1

HCID 578516583-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl esterYield 56.3%

Reagents, catalysts & solvents 3

HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 962WaterSolvent
HCID 5223901,2-DimethoxyetheneSolvent

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

  1. customThe mixture was flushed with N2
  2. temperatureThe reaction mixture was cooled
  3. customsolvent was removed under reduced pressure
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes