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Benzene, 1-bromo-3-nitro- → HCID 67390544, compound

HRID 906214
Notes
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Reaction equation

HRID 906214 reaction equation
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.Br[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([N+:54]([O-:56])=[O:55])[CH:49]=1.Cl.Cl.[CH:59]([N:62]1[CH2:67][C@@H:66]2[CH2:68][C@H:63]1[CH2:64][NH:65]2)([CH3:61])[CH3:60].CC(C)([O-])C.[Na+]>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]>[CH:59]([N:62]1[CH2:67][C@@H:66]2[CH2:68][C@H:63]1[CH2:64][N:65]2[C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([N+:54]([O-:56])=[O:55])[CH:49]=1)([CH3:61])[CH3:60]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11457Benzene, 1-bromo-3-nitro-HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67389593(1S,4S)-2-(propan-2-yl)-2,5-diazabicyclo[2.2.1]heptane dihydrochloride

Product 1

HCID 67390544HCID 67390544, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

A solution of BINAP (0.47 g, 0.75 mmol) and tris(dibenzylideneacetone)dipalladium (0) (0.34 g, 0.37 mmol) in toluene (120 mL) was heated to 90° C. during 15 minutes under nitrogen. The reaction mixture was cooled to 40° C. before adding 1-bromo-3-nitrobenzene (1.89 g, 9.37 mmol), (1S,4S)-2-isopropyl-2,5-diazabicyclo[2.2.1]heptane dihydrochloride (2.0 g, 9.37 mmol) and sodium tert-butoxide (3.14 g, 32.74 mmol). The reaction was heated to 90° C. during 18 hours under nitrogen. After return to room temperature, the reaction was diluted with ethyl acetate and filtered through celite. The filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with a mixture of DCM/7N NH3 in methanol (96/4) to afford the title compound (1.92 g, 78%).

Workup

  1. temperatureThe reaction was heated to 90° C. during 18 hours under nitrogen
  2. filtrationfiltered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel eluting with a mixture of DCM/7N NH3 in methanol (96/4)

Sources & evidence

ORD record
ord-5062982f87b649e18fdc2b7e7420f1f6
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08012983B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes