1,3-Dibromobenzene → HCID 71138417, compound

HRID 1852910Notes

Reaction equation

HRID 1852910 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.[NH:9]1[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]1.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.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.O.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]>[Br:8][C:4]1[CH:3]=[C:2]([N:9]2[CH2:19][CH2:18][CH:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:11][CH2:10]2)[CH:7]=[CH:6][CH:5]=1

Participants

9

Reactant 4

HCID 79271,3-DibromobenzeneHCID 70770Ethyl 4-piperidinecarboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 71138417HCID 71138417, compoundYield 42.7%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,3-dibromobenzene (10 g, 42 mmol) in toluene (424 mL), were added ethyl isonipecotate (6.5 mL, 42 mmol), rac-BINAP (2.0 g, 3.2 mmol), NaOtBu (4.9 g, 51 mmol) and Pd2(dba)3 (0.97 g, 1.1 mmol). The mixture was heated at 80° C. for 4 h and diluted with water and ethyl acetate and separated. The organic phase was dried over unhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 9:1) to give the titled compound (5.6 g, 42%).

Workup

  1. customseparated
  2. dry with materialThe organic phase was dried over unhydrous Na2SO4
  3. customevaporated under reduced pressure
  4. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 9:1)

Sources & evidence

ORD record
ord-260a500110bf437cbec56258203b414c
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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