N-(2-Fluoro-4-iodophenyl)methanesulfonamide → N-(4-Cyano-2-fluorophenyl)methanesulfonamide

HRID 2402313Notes

Reaction equation

HRID 2402313 reaction equation
[F:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[CH:4][C:3]=1[NH:9][S:10]([CH3:13])(=[O:12])=[O:11].[C:14]([Zn]C#N)#[N:15]>CN(C=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:14]([C:6]1[CH:5]=[CH:4][C:3]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:2]([F:1])[CH:7]=1)#[N:15]

Participants

5

Reactant 2

HCID 19785608N-(2-Fluoro-4-iodophenyl)methanesulfonamideHCID 178514179HCID 178514179, compound

Product 1

HCID 15981202N-(4-Cyano-2-fluorophenyl)methanesulfonamideYield 167.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 10A (5.0 g, 16 mmol), dicyanozinc (1.12 g, 9.5 mmol), and Pd(PPh3)4 (0.92 g, 0.79 mmol) in DMF (15 mL) was heated at 80° C. overnight. The mixture was concentrated in vacuo then diluted with EtOAc (400 mL) and washed with brine (3×100 mL). The organic extract was dried (Na2SO4), filtered, and concentrated. The residue was purified by flash chromatography (SiO2, 25-50% Hexanes/EtOAc gradient) to afford the title compound (3.4 g, 99% yield). 1H NMR (300 MHz, DMSO-d6) δ 10.28 (s, 1H), 7.92 (dd, J=10.7, 1.8 Hz, 1H), 7.73-7.56 (m, 2H), 3.31 (s, 3H). MS (ESI; M−H) m/z 213.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with EtOAc (400 mL)
  3. washwashed with brine (3×100 mL)
  4. extractionThe organic extract
  5. dry with materialwas dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (SiO2, 25-50% Hexanes/EtOAc gradient)

Sources & evidence

ORD record
ord-ce18d10cbf3a46c0851ad232aebb2518
Source dataset
uspto-grants-2014_08
Patent number
US08796328B2

Reaction notes

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