3,5-Dibromopyridine → HCID 59777373, compound

HRID 1013074Notes

Reaction equation

HRID 1013074 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:61]1([CH:67]([NH2:71])[CH2:68][CH2:69][CH3:70])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>C1(C)C=CC=CC=1.CCOCC.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]>[Br:8][C:6]1[CH:7]=[C:2]([NH:71][CH:67]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)[CH2:68][CH2:69][CH3:70])[CH:3]=[N:4][CH:5]=1

Participants

8

Reactant 4

HCID 693693,5-DibromopyridineHCID 634876Binap, (A+-)-HCID 36037851-phenylbutan-1-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 59777373HCID 59777373, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a degassed solution of 3,5-dibromopyridine (0.4 g, 1.7 mmol), sodium tert-butoxide (227 mg, 3.6 mmol), tris(dibenzylideneacetone)dipalladium (145 mg, 0.09 mmol) and rac-BINAP (105 mg, 0.2 mmol) in dry toluene (10 mL) was added 1-phenylbutan-1-amine (0.2 mL). The mixture was heated at reflux for 24 h and upon cooling to room temperature was diluted with ether and washed with brine (3×30 mL). The solution was dried (Na2SO4) and concentrated and the residue chromatographed using ethyl acetate-hexane (40:60) as eluant. From the early fractions 97 mg of pure product was obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. washwashed with brine (3×30 mL)
  4. dry with materialThe solution was dried (Na2SO4)
  5. concentrationconcentrated
  6. customthe residue chromatographed

Sources & evidence

ORD record
ord-453eba706ba8470a87c049c94fe88b57
Source dataset
uspto-grants-2011_07
Patent number
US07981900B2

Reaction notes

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