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

HRID 2202832Notes

Reaction equation

HRID 2202832 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 NaH (40% 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, and the resulting mixture was stirred at room temperature overnight. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over MgSO4, and concentrated. The resulting solid was suspended in IPE, stirred for 1 h, and collected by filtration. The crude product was dissolved in EtOAc (1100 ml) at 70° C., and hexane (400 ml) was added while the temperature was maintained at 60° C. Seed crystal was added, and the mixture was stirred at the same temperature for 1 h. Additional hexane (400 ml) was added at 60° C., and the mixture was allowed to cool to room temperature overnight. The precipitate was collected by filtration, washed with hexane/EtOAc (1/1) 3 times, and dried to give the title compound (30.5 g) as a white solid.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. extractionextracted with EtOAc
  3. washThe extract was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. stirringstirred for 1 h
  7. filtrationcollected by filtration
  8. dissolutionThe crude product was dissolved in EtOAc (1100 ml) at 70° C.
  9. additionhexane (400 ml) was added while the temperature
  10. temperaturewas maintained at 60° C
  11. additionSeed crystal was added
  12. stirringthe mixture was stirred at the same temperature for 1 h
  13. additionAdditional hexane (400 ml) was added at 60° C.
  14. temperatureto cool to room temperature overnight
  15. filtrationThe precipitate was collected by filtration
  16. washwashed with hexane/EtOAc (1/1) 3 times
  17. customdried

Sources & evidence

ORD record
ord-01a17516833f4fc3b504cbfa5d4bc1ca
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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