Toluene → HCID 60166861, compound

HRID 473510Notes

Reaction equation

HRID 473510 reaction equation
Cl[C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[F:20][C:21]1[C:27]([F:28])=[C:26]([F:29])[CH:25]=[CH:24][C:22]=1[NH2:23].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C1(C)C=CC=CC=1>CC([O-])=O.CC([O-])=O.[Pd+2].C(O)(C)(C)C>[CH3:16][O:15][C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][CH2:10][C:4]3[CH:3]=[C:2]([NH:23][C:22]4[CH:24]=[CH:25][C:26]([F:29])=[C:27]([F:28])[C:21]=4[F:20])[CH:19]=[CH:18][C:5]=3[C:6](=[O:17])[C:7]=2[CH:14]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 774682,3,4-TrifluoroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 54587822HCID 54587822, compound

Product 1

HCID 60166861HCID 60166861, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

In accordance with general method AA, 0.50 g (1.8 mmol) of 2-chloro-7-methoxy-10,11-dihydrodibenzo[a,d]-cyclohepten-5-one (34), 0.27 g (1.8 mmol) of 2,3,4-trifluoroaniline, 0.05 g (0.22 mmol) of Pd(OAc)2, 0.10 g (0.21 mmol) of 2-(dicyclohexylphosphino)-2′-,4′-,6′-triisopropyl-biphenyl, 0.60 g (6.2 mmol) of Na—O-tert-butylate, 5 ml of toluene and 1 ml of tert-BuOH are used. Reaction time: 1 h. Purification is carried out via flash chromatography (SiO2, hexane/ethyl acetate 8+2). Yield: 72%; melting point: 128° C.

Workup

  1. customReaction time
  2. custom1 h
  3. customPurification

Sources & evidence

ORD record
ord-2fdecca73d8e465699f52db79967f745
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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