O-Phenylenediamine → HCID 45280582, compound

HRID 473452Notes

Reaction equation

HRID 473452 reaction equation
Cl[C:2]1[CH:26]=[CH:25][C:5]2[C:6](=[O:24])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1.[C:27]1([NH2:34])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH2:33].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>[NH2:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[NH:34][C:2]1[CH:26]=[CH:25][C:5]2[C:6](=[O:24])[C:7]3[CH:14]=[C:13]([O:15][CH2:16][CH2:17][N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[CH:12]=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 7243O-PhenylenediamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 23665647Potassium tert-butoxideHCID 67362032HCID 67362032, compound

Product 1

HCID 45280582HCID 45280582, compoundYield 74%

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, 1.0 (9.2 mmol) g of 1,2-phenylenediamine, 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: 74%; C27H29N3O3 (Mr=443.55))

Sources & evidence

ORD record
ord-5e47fda6b818405796d666466f36bea4
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

Loading…