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

HRID 2092616Notes

Reaction equation

HRID 2092616 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:17][O:18][C:19](=[O:38])[C:20]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[C:22]([N+:35]([O-:37])=[O:36])[CH:21]=1>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][O:18][C:19](=[O:38])[C:20]1[CH:21]=[C:22]([N+:35]([O-:37])=[O:36])[CH:23]=[C:24]([C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=2)[CH:25]=1

Participants

6

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 40%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

To a solution of 2-bromo-5-methylpyridine (1.24 g, 7 mmol), Pd(PPh3)4(226 mg, 0.2 mmol) and K3PO4(2.76 g, 13 mmol) in DME/H2O (5 ml/1 ml) was added 3-nitro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (2.00 g, 6.5 mmol) under N2 atmosphere. The mixture was subjected to microwave radiation at 130° C. for 0.5 hours. The reaction mixture was cooled and solvent was evaporated under reduced pressure. The residue was purified by flash-chromatography (CH2Cl2/MeOH) to give 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester as a white solid (700 mg, 40%).

Workup

  1. customat 130° C.
  2. customfor 0.5 hours
  3. temperatureThe reaction mixture was cooled
  4. customsolvent was evaporated under reduced pressure
  5. customThe residue was purified by flash-chromatography (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-d8628d803079494da5400b1f146c4df5
Source dataset
uspto-grants-2013_05
Patent number
US08440708B2

Reaction notes

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