1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea → (S)-Methyl 2-(1-oxo-6-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)propanoate

HRID 403937Notes

Reaction equation

HRID 403937 reaction equation
[CH3:1][O:2][C:3](=[O:38])[C@H:4]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=4)=[O:25])=[CH:19][CH:18]=3)=[CH:13][CH:14]=2)[C:9]1=[O:37])[CH:5](C)C.BrC1C=C2C(CN([C@@H](C)C(OC)=O)C2=O)=CC=1.CC1(C)C(C)(C)OB(C2C=CC(NC(NC3C=CC=C(C(F)(F)F)C=3)=O)=CC=2)O1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[O:37]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[C:12]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24]([NH:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:34])([F:36])[F:35])[CH:28]=4)=[O:25])=[CH:21][CH:22]=3)[CH:11]=2)[CH2:16][N:8]1[C@@H:4]([CH3:5])[C:3]([O:2][CH3:1])=[O:38]

Participants

6

Reactant 3

HCID 161251031-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)ureaHCID 67306227(R)-Methyl-3-methyl-2-(1-oxo-6-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)butanoateHCID 125486231(S)-Methyl 2-(6-bromo-1-oxoisoindolin-2-yl)propanoate

Product 1

HCID 131731531(S)-Methyl 2-(1-oxo-6-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)propanoate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolvent

Procedure

The compound of example 336 was prepared analogous to compound of example 330 by reaction of the compound of example 335, compound of example 327 and Pd(dppf)Cl2: CH2Cl2.

Sources & evidence

ORD record
ord-2c4c7c31117746c4837c7ad1f9fe3e77
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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