Toluene → HCID 10920688, compound

HRID 1465460Notes

Reaction equation

HRID 1465460 reaction equation
CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1.Br[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[CH2:21]([NH:23][CH2:24][CH3:25])[CH3:22]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C(Cl)(Cl)Cl.[Pd].[Pd].C(OCC)(=O)C.O>[CH2:21]([N:23]([CH2:24][CH3:25])[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)[CH3:22]

Participants

8

Reactant 4

HCID 1140TolueneHCID 8021DiethylamineHCID 122863-BromopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 10920688HCID 10920688, compoundYield 36.4%

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4,5-bis(diphenylphosphino)-9,9′-dimethylxanthene (521 mg, 0.90 mmol), tris(dibenzylideneacetone)dipalladium (0)-chloroform adduct (311 mg, 0.30 mmol), sodium t-butoxide (2.16 g, 23 mmol) and anhydrous toluene (37 ml) were added 3-bromopyridine (1.5 ml, 15 mmol) and diethylamine (1.9 ml, 18.0 mmol). The mixture was heated to 70° C., and the mixture was stirred for 3 hrs and at room temperature overnight. Water and ethyl acetate were added to the reaction mixture. The mixture was stirred, stood still and partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→2:1) to give N,N-diethylpyridin-3-amine (820 mg, yield 36%) as a brown oil.

Workup

  1. stirringThe mixture was stirred
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1→2:1)

Sources & evidence

ORD record
ord-5c193408bd574d5a95464e31b952091a
Source dataset
uspto-grants-2015_04
Patent number
US08999989B2

Reaction notes

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