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

HRID 403973Notes

Reaction equation

HRID 403973 reaction equation
CC(C)[C@@H]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([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:14]=2)[C:9]1=[O:37])C(OC)=O.BrC1C=C2C(=CC=1)C(=O)N([CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])C2.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][C:13]([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:34])([F:35])[F:36])[CH:28]=4)=[O:25])=[CH:19][CH:18]=3)=[CH:12][CH:11]=2)[CH2:16][N:8]1[CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53]

Participants

6

Reactant 3

HCID 161251031-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)ureaHCID 67307314Ethyl 3-(5-bromo-1-oxoisoindolin-2-yl)propanoateHCID 131731536(R)-Methyl 3-methyl-2-(1-oxo-5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)isoindolin-2-yl)butanoate

Product 1

HCID 53302443Ethyl 3-(1-oxo-5-(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 378 was prepared analogous to compound of example 360 by reaction of the compound of example 377, compound of example 357 and Pd(dppf)Cl2: CH2Cl2.

Sources & evidence

ORD record
ord-76eaead9fcfd49ddb7f597c677d7ee7c
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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