O-Phenylenediamine → (S)-2-(2-Aminophenylamino)-8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

HRID 473459Notes

Reaction equation

HRID 473459 reaction equation
Cl[C:2]1[CH:26]=[CH:25][C:5]2[C:6](=[O:24])[C:7]3[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]4)=[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].P.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1.C(O)(C)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[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]=[CH:13][C:12]([O:15][CH2:16][C@H:17]4[CH2:21][O:20][C:19]([CH3:23])([CH3:22])[O:18]4)=[CH:11][C:8]=3[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 7243O-PhenylenediamineHCID 24404PhosphineHCID 67360028HCID 67360028, compoundHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 45280586(S)-2-(2-Aminophenylamino)-8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one

Reagents, catalysts & solvents 3

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

Procedure

For the synthesis of the title compound, 0.91 g (0.0024 mol) of (S)-2-chloro-8-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-10,11-dihydrodibenzo[a,d]cyclohepten-5-one, 1.00 g (0.0092 mol) of phenylenediamine, 2 spatula tips of Pd(OAc)2, 0.18 g of phosphine ligand and 1.60 g (0.0166 mol) of NaOtert-Bu in 10 ml of toluene and 2 ml of tert-BuOH are reacted by method O.

Sources & evidence

ORD record
ord-628a0bc5e2b94995a49323e2d7942984
Source dataset
uspto-grants-2014_01
Patent number
US08633312B2

Reaction notes

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