5-Bromo-2-nitropyridine → HCID 131731576, compound

HRID 404029Notes

Reaction equation

HRID 404029 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](C3C=CC([N+]([O-])=O)=CN=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5].CC(C)[C@H](N1CC2C(=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)C1=O)C(OC)=O.Br[C:56]1[CH:57]=[N:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=1>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:56]3[CH:57]=[N:58][C:59]([N+:62]([O-:64])=[O:63])=[CH:60][CH:61]=3)=[CH:13][CH:14]=2)[C:9]1=[O:26])[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 3

HCID 8176205-Bromo-2-nitropyridineHCID 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 131731576HCID 131731576, compoundYield 33%

Reagents, catalysts & solvents 2

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

Procedure

The compound of example 489 was prepared analogous to the compound of example 391 by reaction of the compound of example 390, 3-bromo-6-nitro pyridine and Pd(dppf)Cl2: CH2Cl2.

Sources & evidence

ORD record
ord-898ff3be29174d2c8b92568f086f8701
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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