Dimethylformamide → 2,3-Dichloro-N-[5-cyano-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

HRID 1443995Notes

Reaction equation

HRID 1443995 reaction equation
Br[C:2]1[N:3]=[C:4]([O:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)[C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[N:6][CH:7]=1.[CH3:28][N:29](C)C=O>C(OCC)(=O)C.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.[C-]#N.[Zn+2].[C-]#N>[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[C:4]([O:20][CH2:21][C:22]2[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=2)=[N:3][C:2]([C:28]#[N:29])=[CH:7][N:6]=1)(=[O:11])=[O:10]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 10239030N-[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide

Product 1

HCID 101512992,3-Dichloro-N-[5-cyano-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl]-2,3-dichlorobenzenesulphonamide (Example 34) (0.15 g), tetrakis(triphenylphosphine)palladium(0) (0.04 g) and zinc cyanide (0.03 g) in N,N-dimethylformamide (5.0 mL) was heated at 70° C. After 5 h, the mixture was diluted with ethyl acetate (30 mL) and washed with 5% aqueous citric acid (5 mL), dried (MgSO4) and evaporated. Chromatography on silica gel eluting with ethyl acetate/isohexane mixtures containing 1% acetic acid gave the title compound as a white solid (0.058 g).

Workup

  1. washwashed with 5% aqueous citric acid (5 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. additionChromatography on silica gel eluting with ethyl acetate/isohexane mixtures containing 1% acetic acid

Sources & evidence

ORD record
ord-cf0362a998214f3588945897d9972a21
Source dataset
uspto-grants-2010_02
Patent number
US07662825B2

Reaction notes

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