Diisopropylethylamine → N-(5-Iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamide

HRID 2202985Notes

Reaction equation

HRID 2202985 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.Br[CH:20]([C:22](=[O:25])[CH2:23][CH3:24])[CH3:21].C(N(CC)C(C)C)(C)C>C1COCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5](=[N: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:20]([C:22](=[O:25])[CH2:23][CH3:24])[CH3:21])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5450922-Bromo-3-pentanoneHCID 21772024N-(5-Iodo-pyridin-2-YL)-4-methyl-benzenesulfonamide

Product 1

HCID 131735782N-(5-Iodo-1-(3-oxopentan-2-yl)pyridin-2(1H)-ylidene)-4-methylbenzenesulfonamideYield 43.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(5-iodopyridin-2-yl)-4-methylbenzenesulfonamide (3 g) and 2-bromopentan-3-one (3.3 g) in THF (50 ml) was added N,N-diisopropylethylamine (5.6 ml) at 0° C., and the resulting mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated in vacuo, poured into saturated NaHCO3 solution and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, concentrated in vacuo and purified by silica gel column chromatography (hexane/EtOAc) to afford the title compound (1.6 g) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionpoured into saturated NaHCO3 solution
  3. extractionextracted with EtOAc
  4. washThe extract was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. custompurified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-a800d30038b24c689b16a0103d906100
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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