Sodium Carbonate → HCID 22473536, compound

HRID 2183985Notes

Reaction equation

HRID 2183985 reaction equation
Br[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH3:11].B1([C:18]2[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=2)OCCCO1.C([O-])([O-])=O.[Na+].[Na+]>CCO.C1(C)C=CC=CC=1.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>[CH3:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 821892-Bromo-4-nitrotolueneHCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridine

Product 1

HCID 22473536HCID 22473536, compoundYield 103.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 2-bromo-4-nitrotoluene (3 g, 13.0 mmol) and pyridine-3-boronic acid-1,3-propanediol cyclic ester (2.72 g, 16.7 mmol) in EtOH (30 ml) and toluene (30 ml) together with 2N Na2CO3 solution (13.9 ml) was degassed with a stream of N2 for 10 min. Tetrakis(triphenylphosphine)palladium(0) (0.3 g, 0.26 mmol) was added and the reaction heated at reflux for 4 h. The mixture was concentrated under reduced pressure to remove the organic solvents and water (100 ml) was added. The organics were extracted with EtOAc (200 ml) and then washed with brine (75 ml), dried (MgSO4), and concentrated under reduced pressure while dry loading onto silica. The resulting crude residue was purified by column chromatography on silica, using 60% diethyl ether in hexane as the eluent, to yield 3-(2-methyl-5-nitrophenyl)pyridine (2.87 g, 99%): δH (360 MHz, CDCl3) 2.38 (3H, s), 7.36-7.50 (2H, m), 7.67 (1H, dt, J 7.9 and 1.9), 8.10 (1H, d, J 2.4), 8.61 (1H, d, J 1.8), 8.67 (1H, dd, J 4.8 and 1.5).

Workup

  1. customwas degassed with a stream of N2 for 10 min
  2. temperaturethe reaction heated
  3. temperatureat reflux for 4 h
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customto remove the organic solvents and water (100 ml)
  6. additionwas added
  7. extractionThe organics were extracted with EtOAc (200 ml)
  8. washwashed with brine (75 ml)
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under reduced pressure
  11. customwhile dry loading onto silica
  12. customThe resulting crude residue was purified by column chromatography on silica

Sources & evidence

ORD record
ord-9320c735e2c342f7beb43593f4cca018
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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