Cesium carbonate → HCID 67248827, compound

HRID 1190893Notes

Reaction equation

HRID 1190893 reaction equation
Br[C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[C:6](Br)[CH:7]=1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P([C:52]2[CH:57]=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:64][N:65]1[CH2:70][CH2:69][NH:68][CH2:67][CH2:66]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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:64][N:65]1[CH2:70][CH2:69][N:68]([C:2]2[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[C:6]([N:68]3[CH2:52][CH2:57][N:65]([CH3:64])[CH2:66][CH2:67]3)[CH:7]=2)[CH2:67][CH2:66]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 2387111,3-dibromo-5-nitrobenzeneHCID 634876Binap, (A+-)-

Product 1

HCID 67248827HCID 67248827, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

In a oven-dried flask and under a nitrogen atmosphere, were placed 3,5-dibromonitrobenzene (500 mg, 1.78 mmol), (+/−) BINAP (110 mg, 0.1 eq), Cs2CO3 (1.62 g, 3 eq), Pd2dba3 (81 mg, 0.11 eq) and 10 mL of dry 1,4-dioxane. N-Methylpiperazine (0.47 mL, 2.4 eq) was added and the mixture was stirred at 90° C. for 48 h. The solution was filtered through a celite pad and evaporated. The residue was purified by flash chromatography on silica gel (DCM/MeOH/NH4OH//95/5/1) to yield expected compound as an orange solid (258 mg, 45% yield). m/z (MALDI-TOF) 320.2 [M+H]+;

Workup

  1. customIn a oven-dried flask and under a nitrogen atmosphere, were placed
  2. filtrationThe solution was filtered through a celite pad
  3. customevaporated
  4. customThe residue was purified by flash chromatography on silica gel (DCM/MeOH/NH4OH//95/5/1)

Sources & evidence

ORD record
ord-51d94bd0df9140beb02af5a5ef2f4d49
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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