Potassium Carbonate → 2-[2-(4-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide

HRID 660059

Reaction equation

HRID 660059 reaction equation
C([O-])([O-])=O.[K+].[K+].[SH:7][C:8]1[N:22]=[CH:21][CH:20]=[CH:19][C:9]=1[C:10]([NH:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)=[O:11].Cl[CH2:24][CH2:25][S:26]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)(=[O:28])=[O:27].C(Cl)Cl.CC(=O)OCC>CN(C=O)C>[F:35][C:32]1[CH:33]=[CH:34][C:29]([S:26]([CH2:25][CH2:24][S:7][C:8]2[N:22]=[CH:21][CH:20]=[CH:19][C:9]=2[C:10]([NH:12][CH2:13][C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[O:11])(=[O:28])=[O:27])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 27365051-(2-Chloroethanesulfonyl)-4-fluorobenzeneHCID 21226138Dichloromethane ethylacetateHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

Product 1

HCID 687268732-[2-(4-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamideYield 48%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

303 mg (2.2 mmol) of K2CO3 were added to a solution of 500 mg (2.0 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (5 ml), and stirring was carried out for 30 min at RT. 445 mg (2.0 mmol) of 1-(2-chloroethylsulfonyl)-4-fluorobenzene were then added and stirring was continued for a further 2 days at RT. The mixture was then concentrated in vacuo, the residue was taken up in EA, and 1M aqueous NaHCO3 solution was added. The phases were separated and the aqueous phase was extracted with EA. The combined organic phases were dried over MgSO4, filtered through silica gel and concentrated in vacuo. CC (DCM/EA 4:1) of the residue yielded 365 mg (0.84 mmol, 48%) of 2-[2-(4-fluorophenyl)sulfonylethylthio]-N-(2-thienylmethyl)-nicotinamide. MS: m/z 437.0 [M+H]+

Workup

  1. stirringstirring
  2. waitwas continued for a further 2 days at RT
  3. concentrationThe mixture was then concentrated in vacuo
  4. addition1M aqueous NaHCO3 solution was added
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with EA
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered through silica gel
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-107a00e5d1014a2d85e5395f9e05ba4b
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Linked notes

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