Water → 3-(3-Nitrophenyl)pyridine

HRID 1696530Notes

Reaction equation

HRID 1696530 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=1.C([O-])([O-])=O.[Na+].[Na+].O>COCCOC.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>[N+:8]([C:4]1[CH:3]=[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)[CH:7]=[CH:6][CH:5]=1)([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 125741-Iodo-3-nitrobenzeneHCID 27343783-Pyridinylboronic acid

Product 1

HCID 121813273-(3-Nitrophenyl)pyridineYield 78.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a degassed solution of 1-iodo-3-nitrobenzene (0.35 g, 1.4 mmol) in DME (5 mL) was added Pd(PPh3)4 (0.08 g, 10% mol). After stirring for 5 min, 3-pyridylboronic acid (0.2 g, 1.65 mmol) and 2M Na2CO3 (1 mL) solution were added. After refluxing for 16 h under an Ar atmosphere, the reaction mixture was poured into H2O (15 mL) and extracted with EtOAc (2×30 mL). The combined organic extracts were washed with brine, dried (Na2SO4), concentrated and purified via column chromatography to yield 3-(3-nitrophenyl)pyridine (0.22 g, 78%) as a white solid. 1H NMR (CDCl3): δ 8.94 (brs, 1H), 8.73 (brs, 1H), 8.48 (t, J=1.6 Hz, 1H), 8.32-8.29 (m, 1H), 7.98-7.93 (m, 2H), 7.72-7.68 (m, 1H), 7.48 (brs, 1H); Exact mass: 200.0, Found: 201.0 (M+1)+.

Workup

  1. temperatureAfter refluxing for 16 h under an Ar atmosphere
  2. extractionextracted with EtOAc (2×30 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-d7cbad21368b400cbce8adac8855e98f
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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