2,4-Difluoroaniline → HCID 45280530, compound

HRID 473449Notes

Reaction equation

HRID 473449 reaction equation
Cl[C:2]1[CH:24]=[CH:23][C:5]2[C:6](=[O:22])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][O:18]C(=O)C)[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[F:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH2:28].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.CC([O-])(C)C.[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].CC(O)(C)C.C1(C)C=CC=CC=1>[F:25][C:26]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:27]=1[NH:28][C:2]1[CH:24]=[CH:23][C:5]2[C:6](=[O:22])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][OH:18])[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 67497507HCID 67497507, compound

Product 1

HCID 45280530HCID 45280530, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6386tert-ButanolSolvent

Procedure

For the preparation of the compound by method C, 0.62 g (1.8 mmol) of 2-chloro-7-(2-acetoxyethoxy)-10,11-dihydrodibenzo[a,d]-cyclohepten-5-one, 0.25 g (1.9 mmol) of 2,4-difluoroaniline, 0.05 g (0.22 mmol) of Pd(OAc)2, 0.10 g (0.21 mmol) of 2-(dicyclohexylphosphino)-2′-,4′-,-6′-triisopropyl-biphenyl, 0.70 g (6.2 mmol) of KOt-Bu, 5 ml of toluene and 1 ml of t-BuOH are used. Yield: 34%; C23H19F2NO3 (Mr=395.41)

Sources & evidence

ORD record
ord-9a0c1d537d1540d99aa5b72aa738dd25
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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