Potassium Carbonate → 3-(Pyridin-3-yl)aniline

HRID 49814

Reaction equation

HRID 49814 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.Br[C:13]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[NH2:16].C(=O)([O-])[O-].[K+].[K+]>O.C(COC)OC.C(OCC)(=O)C.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:6]1[CH:7]=[CH:8][CH:9]=[C:4]([C:13]2[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=2)[NH2:16])[CH:5]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 115623-BromoanilineHCID 6428513-(Diethylboryl)pyridine

Product 1

HCID 4595213-(Pyridin-3-yl)anilineYield 95.8%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of diethyl 3-pyridylborane (16.3 g, 0.1 mol), 3-bromoaniline (12.2 ml, 0.11 mol), potassium carbonate (45.8 g, 0.33 mol) and tetrakis(triphenylphosphine)palladium(0) (80 mg) in a mixture of water (40 ml) and dimethoxyethane (80 ml) is heated to 80° C. under a stream of nitrogen over night. After cooling the mixture is diluted with water and ethyl acetate and filtered through a fluted filterpaper. The layers are separated. The aqueous layer is extracted once with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated under reduced pressure. The residue is dissolved in ethanol. Water is added and the mixture is evaporated to dryness. This residue crystallizes upon trituration with ice-cold water. The crystals are collected, dried and washed with petroleum ether to afford pure 2p (16.3 g, 87%). Mp 75-76° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationfiltered through a fluted filterpaper
  3. customThe layers are separated
  4. extractionThe aqueous layer is extracted once with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue is dissolved in ethanol
  8. additionWater is added
  9. customthe mixture is evaporated to dryness
  10. customThis residue crystallizes upon trituration with ice-cold water
  11. customThe crystals are collected
  12. customdried
  13. washwashed with petroleum ether

Sources & evidence

ORD record
ord-738a4a8fa5094e339d0e1666c336bba9
Source dataset
uspto-grants-2004_03
Patent number
US06710044B2

Linked notes

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