Water → 3-(3-Nitro-4-(phenylsulfonyl)phenyl)pyridine

HRID 72638Notes

Reaction equation

HRID 72638 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](B(O)O)[CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].I[C:17]1[CH:22]=[CH:21][C:20]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])=[C:19]([N+:32]([O-:34])=[O:33])[CH:18]=1.O>C(O)C.O>[N+:32]([C:19]1[CH:18]=[C:17]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:22]=[CH:21][C:20]=1[S:23]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)(=[O:25])=[O:24])([O-:34])=[O:33]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 680147904-Iodo-2-nitro-1-(phenylsulfonyl)-benzene

Product 1

HCID 680147913-(3-Nitro-4-(phenylsulfonyl)phenyl)pyridineYield 70.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

Argon was passed through a mixture of 3-pyridineboronic acid (187 mg, 1.53 mmol) and Na2CO3 (408 mg, 3.84 mmol) in water ethanol (water 3.74 ml, ethanol 14.96 ml) at stirring at 90° C. for 30 min and cooled to 80° C. 4-Iodo-2-nitro-1-(phenylsulfonyl)-benzene 4(3) (734 mg, 1.9 mmol) was added to the reaction mixture in argon current, inert gas was passed for another 10 min, then bis-triphenylphosphinepalladium dichloride (34 mg) was added and argon was passed for additional 5 min. The reaction mixture was stirred for 2 h at 85° C. in argon atmosphere, then, cooled, water was added, and precipitated solid was filtered off. The reaction product was extracted from mother liquor with CH2Cl2, organic layer was dried over Na2SO4, filtered and evaporated to dryness. The residue was suspended in CH2Cl2, filtered off, mother liquor was evaporated, the residue washed with diethyl ether, it gave 460 mg (70.5%) of 3-(3-nitro-4-(phenylsulfonyl)phenyl)pyridine 5(1).

Workup

  1. temperaturecooled to 80° C
  2. waitinert gas was passed for another 10 min
  3. waitargon was passed for additional 5 min
  4. stirringThe reaction mixture was stirred for 2 h at 85° C. in argon atmosphere
  5. temperaturecooled
  6. customprecipitated solid
  7. filtrationwas filtered off
  8. extractionThe reaction product was extracted from mother liquor with CH2Cl2, organic layer
  9. dry with materialwas dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated to dryness
  12. filtrationfiltered off
  13. custommother liquor was evaporated
  14. washthe residue washed with diethyl ether, it

Sources & evidence

ORD record
ord-0416002001de41a98792e292d69eb896
Source dataset
uspto-grants-2014_09
Patent number
US08829002B2

Reaction notes

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