Water → N-(1-(1-Cyclopropyl-1-oxopropan-2-yl)-5-iodopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide

HRID 60381Notes

Reaction equation

HRID 60381 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[H-].[Na+].Br[CH:22]([CH3:28])[C:23]([CH:25]1[CH2:27][CH2:26]1)=[O:24].O>CN(C=O)C>[CH:25]1([C:23](=[O:24])[CH:22]([N:6]2[CH:7]=[C:2]([I:1])[CH:3]=[CH:4][C:5]2=[N:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH3:28])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 21772024N-(5-Iodo-pyridin-2-YL)-4-methyl-benzenesulfonamideHCID 450808052-Bromo-1-cyclopropylpropan-1-one

Product 1

HCID 131735781N-(1-(1-Cyclopropyl-1-oxopropan-2-yl)-5-iodopyridin-2(1H)-ylidene)-4-methylbenzenesulfonamideYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(5-iodopyridin-2-yl)-4-methylbenzenesulfonamide (33.1 g) in DMF (400 mL) was added sodium hydride (60% oil dispersion, 3.89 g) at 0° C., and the mixture was stirred at room temperature for 30 min. Then 2-bromo-1-cyclopropylpropan-1-one (23.5 g) was added to the obtained mixture, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo. The resulting solid was suspended in diisopropyl ether, the suspension was stirred for 1 hr, and the solid was collected by filtration. The obtained solid was dissolved in ethyl acetate (1100 mL) at 70° C., and hexane (400 mL) was dropwise added at 60° C. The mixture was allowed to cool to room temperature overnight. The resulting precipitate was collected by filtration, washed with hexane/ethyl acetate (1/1) 3 times, and dried to give the title compound (30.5 g) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe obtained organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. stirringthe suspension was stirred for 1 hr
  7. filtrationthe solid was collected by filtration
  8. dissolutionThe obtained solid was dissolved in ethyl acetate (1100 mL) at 70° C.
  9. additionhexane (400 mL) was dropwise added at 60° C
  10. temperatureto cool to room temperature overnight
  11. filtrationThe resulting precipitate was collected by filtration
  12. washwashed with hexane/ethyl acetate (1/1) 3 times
  13. customdried

Sources & evidence

ORD record
ord-24460f0c3d8649ab9dbbf6b688a11504
Source dataset
uspto-grants-2016_09
Patent number
US09440987B2

Reaction notes

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