5-Bromo-2-iodobenzonitrile → 5-Bromo-2-pyridin-3-ylbenzonitrile

HRID 562901Notes

Reaction equation

HRID 562901 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](OB(O)O)[CH:12]=1>C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

6

Reactant 2

HCID 70208745-Bromo-2-iodobenzonitrileHCID 184153773-Pyridylboric acid

Product 1

HCID 669952315-Bromo-2-pyridin-3-ylbenzonitrile

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
100 °C

Procedure

5-Bromo-2-iodobenzonitrile and 3-pyridylboric acid were dissolved in a mixture solution of aqueous 2 M sodium carbonate solution and toluene, then tetrakis(triphenylphosphine)palladium was added thereto, and the mixture was heated, stirred with heating in an argon atmosphere at 100° C. for 3 days to obtain 5-bromo-2-pyridin-3-ylbenzonitrile. EI: 258, 260.

Workup

  1. temperaturethe mixture was heated

Sources & evidence

ORD record
ord-1c41b8fe666e4937af3a0fd2585c2cc8
Source dataset
uspto-grants-2011_11
Patent number
US08067446B2

Reaction notes

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