Bromobenzene → HCID 27441130, compound

HRID 2416648Notes

Reaction equation

HRID 2416648 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C@H:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+].C(=O)([O-])O.[Na+]>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].C1(C)C=CC=CC=1>[C:2]1([N:13]2[CH2:12][CH2:11][NH:10][C@@H:9]([CH3:8])[CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7961BromobenzeneHCID 516892Sodium BicarbonateHCID 634876Binap, (A+-)-HCID 27342192-Methylpiperazine, (S)-HCID 23676156Sodium t-butoxide

Product 1

HCID 27441130HCID 27441130, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of bromobenzene (300 mg), (S)-2-methylpiperazine (230 mg), (S)-(−)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (48 mg), sodium tert-butoxide (266 mg), tris-(dibenzylideneacetone)dipalladium(0) (26 mg) and toluene (15 ml) was stirred at 100° C. for 4 hours under a nitrogen atmosphere. The mixture was cooled to room temperature and saturated aqueous sodium hydrogencarbonate solution was added thereto. The organic layer was separated, washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The obtained crude product was purified by silica gel column chromatography (chloroform-methanol 20:1) to give the title compound in a pure form.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (chloroform-methanol 20:1)

Sources & evidence

ORD record
ord-36833c21b2ce479a9400a71f1b09c767
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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