4-Bromobiphenyl → HCID 9817097, compound

HRID 991991Notes

Reaction equation

HRID 991991 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.CC([O-])(C)C.[Na+].C(NC(C)C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2].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>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:21]2[CH:22]=[CH:23][C:18]([C:15]3[CH:16]=[CH:17][CH:12]=[CH:13][CH:14]=3)=[CH:19][CH:20]=2)[NH2:10])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 71014-BromobiphenylHCID 7912DiisopropylamineHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 23676156Sodium t-butoxide

Product 1

HCID 9817097HCID 9817097, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-Catalyst

Conditions

Temperature
50 °C

Procedure

4-Fluorophenylhydrazine hydrochloride (1-2 equiv., 0.6 mmol, 98 mg), 4-bromobiphenyl (1.0 equiv., 0.5 mmol, 117 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 mg) and diisopropylamine (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 50° C. under argon for 7 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 white solid (110 mg, 0.39 mmol, 79% 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-095324747c1e458cb605468c6837b294
Source dataset
uspto-grants-2002_10
Patent number
US06465693B2

Reaction notes

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