Sodium Carbonate → 5-Bromo-2-(3-methoxyphenyl)-3-nitropyridine

HRID 1431372Notes

Reaction equation

HRID 1431372 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]([O:13][CH3:12])[CH:19]=2)=[N:3][CH:4]=1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 2984702,5-Dibromo-3-nitropyridineHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 596314285-Bromo-2-(3-methoxyphenyl)-3-nitropyridine

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 2,5-dibromo-3-nitropyridine (0.2621 g, 0.930 mmol), 3-methoxyphenylboronic acid (0.155 g, 1.02 mmol), tetrakis(triphenylphosphine)-palladium (0.076 g, 0.065 mmol), and 2.0M sodium carbonate (2.4 mL, 4.80 mmol) in toluene (3.0 mL) and ethanol (1.0 mL) was heated to 70° C. After 2.5 h, the reaction was cooled to rt then diluted with water. After extraction with EtOAc, the organic extraction was dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified on silica gel (0-20% EtOAc in hexanes) to afford a yellow solid as 5-bromo-2-(3-methoxyphenyl)-3-nitropyridine. 1H NMR (400 MHz, CDCl3) δ ppm 8.91 (1H, d, J=2.2 Hz), 8.27 (1H, d, J=2.2 Hz), 7.42 (1H, m), 7.14 (3H, m), 3.86 (3H, s).

Workup

  1. temperaturethe reaction was cooled to rt
  2. extractionAfter extraction with EtOAc
  3. extractionthe organic extraction
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration
  6. customthe residue was purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-b4f730e4dda54618af9f0b9199ac54fd
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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