1,4-Dibromobenzene → HCID 66861405, compound

HRID 253014Notes

Reaction equation

HRID 253014 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[Na+].[Br:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C.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.[Pd].[Pd]>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:18]2[CH:19]=[CH:20][C:15]([Br:14])=[CH:16][CH:17]=2)[CH:3]=1

Participants

7

Reactant 3

HCID 78041,4-DibromobenzeneHCID 100093-AminopyridineHCID 23676156Sodium t-butoxide

Product 1

HCID 66861405HCID 66861405, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-aminopyridine (200 mg, 2.1 mmol) and 304 mg (3.2 mmol) of sodium tert-butoxide were added to 502 mg (2.1 mmol) of 1,4-dibromobenzene, 127 mg (0.21 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylsantene, and 97 mg (0.11 mmol) of tris(dibenzylideneacetone)dipalladium in toluene (15 ml), and the mixture was stirred at 100° C. for 3 hr. The reaction solution was diluted with 20 ml of ethyl acetate, and the insolubles were filtered through a chromato-disk. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give 312 mg (yield 50%) of a mixture of the title compound with a debromination product thereof (about 3.5:1).

Workup

  1. filtrationthe insolubles were filtered through a chromato-disk
  2. concentrationThe filtrate was concentrated under the reduced pressure
  3. customthe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5dfa66d116af45bd93c7720afa7070db
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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