Potassium Carbonate → HCID 86679143, compound

HRID 1774774Notes

Reaction equation

HRID 1774774 reaction equation
Cl[CH2:2][CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][S:5]1(=[O:10])=[O:9].[Br:11][C:12]1[CH:13]=[C:14]([OH:18])[CH:15]=[N:16][CH:17]=1.C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O>[Br:11][C:12]1[CH:17]=[N:16][CH:15]=[C:14]([O:18][CH2:2][CH2:3][N:4]2[CH2:8][CH2:7][CH2:6][S:5]2(=[O:10])=[O:9])[CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 5995293-Bromo-5-hydroxypyridineHCID 43620016HCID 43620016, compound

Product 1

HCID 86679143HCID 86679143, compoundYield 20.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(2-chloro-ethyl)-isothiazolidine-1,1-dioxide (0.046 g, 0.253 mmol) and 5-bromopyridin-3-ol (0.04 g, 0.230 mmol) in DMF (1 mL) was added K2CO3 (0.064 g, 0.46 mmol), followed by KI (0.008 g, 0.046 mmol) and the reaction mixture was heated to 60° C. and stirred over night. The mixture was diluted with EtOAc, poured into a sat. NaHCO3 solution (5 mL) and the aqueous layer was extracted with EtOAc (2×10 mL). Combined organics were washed with brine, dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 5% MeOH-DCM gradient to give the title compound (0.015 g, 20%) as a yellow oil which was used with no further purification. MS: 321.3 and 323.2 (M+H+).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc (2×10 mL)
  2. washCombined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a 0 to 5% MeOH-DCM gradient

Sources & evidence

ORD record
ord-54613d83df694766954cc83a88e85653
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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