4-Bromobiphenyl → HCID 9817097, compound
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]=1Participants
7
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 (a 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
- customdried test tube which
- customwas capped with a septum
- custompurged briefly with argon (a 1 min.), and
- temperatureThe reaction was then cooled to room temperature
- additiondiluted with Et2O (2 mL)
- filtrationfiltered through Celite
- concentrationconcentrated under vacuum
- customThe crude mixture was purified by flash column chromatography (10% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-f6258989e71b46a093275c8e1d641fad
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235936B1
Reaction notes
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