Phenylhydrazine → HCID 12237734, compound

HRID 991992Notes

Reaction equation

HRID 991992 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=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+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH2:8])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 7516PhenylhydrazineHCID 7806p-BromochlorobenzeneHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 12237734HCID 12237734, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
80 °C

Procedure

Phenylhydrazine (1.2 equiv., 0.6 mmol, 0.06 mL), 4-chlorobromobenzene (1.0 equiv., 0.5 mmol, 96 mg), Pd(OAc)2 (0.05 equiv., 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), NaOtBu (1.4 equiv., 0.7 mmol, 67 mug) and dilsopropylamine (2 mL) were added to an oven dried test tube which was capped with a septum and purged briefly with argon (˜1 min.), and then heated to 80° C. under argon for 2.5 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (10% EtOAc/Hex) to give the title product as a yellow oil (42 mg, 0.19 mmol, 39% yield).

Workup

  1. customdried test tube which
  2. customwas capped with a septum
  3. custompurged briefly with argon (˜1 min.)
  4. temperatureThe reaction was then cooled to room temperature
  5. additiondiluted with Et2O (2 mL)
  6. filtrationfiltered through Celite
  7. concentrationconcentrated under vacuum
  8. customThe crude mixture was purified by flash column chromatography (10% EtOAc/Hex)

Sources & evidence

ORD record
ord-d30fa0c20cf34c5da5e32460634b5ce5
Source dataset
uspto-grants-2002_10
Patent number
US06465693B2

Reaction notes

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