1-Bromo-2-methyl-4-nitrobenzene → HCID 131731570, compound

HRID 404019Notes

Reaction equation

HRID 404019 reaction equation
[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19]N=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].[CH3:28][CH:29](C)[C@H](N1CC2C(=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)C1=O)C(OC)=O.BrC1C=CC([N+]([O-])=O)=CC=1C>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>[CH3:1][CH:2]([CH3:27])[C@H:3]([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][C:12]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:28]=3[CH3:29])=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 2516721-Bromo-2-methyl-4-nitrobenzeneHCID 123866646(S)-Methyl 3-methyl-2-(1-oxo-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-2-yl)butanoateHCID 131731547(S)-Methyl 3-methyl-2-(6-(5-nitropyridin-2-yl)-1-oxoisoindolin-2-yl)butanoate

Product 1

HCID 131731570HCID 131731570, compoundYield 75%

Reagents, catalysts & solvents 2

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

Procedure

The compound of example 465 was prepared analogous to the compound of example 391 by reaction of the compound of example 390, 1-bromo-2-methyl-4-nitro benzene and Pd(dppf)Cl2: CH2Cl2.

Sources & evidence

ORD record
ord-da80050a7fb8441c9110bbf2d6d00137
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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