2,4-Difluoroaniline → HCID 45280531, compound

HRID 473451Notes

Reaction equation

HRID 473451 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[C:20]3[CH2:19][CH2:18][C:17]4[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=4[C:15](=[O:25])[C:14]=3[CH:13]=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:26][C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH2:29].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:26][C:27]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:28]=1[NH:29][C:22]1[CH:23]=[CH:24][C:16]2[C:15](=[O:25])[C:14]3[CH:20]=[C:10]([O:9][CH2:8][CH2:7][N:1]4[CH2:2][CH2:3][O:4][CH2:5][CH2:6]4)[CH:11]=[CH:12][C:13]=3[CH2:19][CH2:18][C:17]=2[CH:21]=1

Participants

8

Reactant 4

HCID 97092,4-DifluoroanilineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 86664808HCID 86664808, compound

Product 1

HCID 45280531HCID 45280531, compoundYield 76%

Reagents, catalysts & solvents 3

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

Procedure

For the preparation of the compound by method C, 0.67 g (1.8 mmol) of 2-chloro-7-(2-morpholin-4-yl-ethoxy-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: 76%; C24H21F2NO4 (Mr=425.44)

Sources & evidence

ORD record
ord-d48963e4c1b14cb0bb253bd38ebca689
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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