Potassium Carbonate → 2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amide

HRID 1925542Notes

Reaction equation

HRID 1925542 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].Br[CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1>CN(C=O)C>[F:33][C:30]1[CH:31]=[CH:32][C:27]([CH2:26][CH2:25][CH2:24][S:7][C:8]2[C:9]([C:10]([NH:12][CH2:13][C:14]3[S:15][CH:16]=[CH:17][CH:18]=3)=[O:11])=[CH:19][CH:20]=[CH:21][N:22]=2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 147371331-(3-Bromopropyl)-4-fluorobenzeneHCID 1785230482-mercapto-N-(thiophen-2-ylmethyl)nicotinamide

Product 1

HCID 469088252-[3-(4-fluorophenyl)-propylsulfanyl]-N-(thiophen-2-yl-methyl)-pyridine-3-carboxylic acid amideYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

227 mg (1.65 mmol) of K2CO3 were added to a solution of 375 mg (1.5 mmol) of 2-mercapto-N-(thiophen-2-ylmethyl)nicotinamide in DMF (6 ml) and stirring was carried out for 1 h at RT. 325 mg (1.5 mmol) of 1-(3-bromopropyl)-4-fluorobenzene were then added and stirring was carried out for a further 16 h at RT. The mixture was then concentrated in vacuo and the residue was taken up in an EA/water mixture. The organic phase was separated off and the aqueous phase was extracted again with EA. The combined organic phases were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by means of CC (EA/hex 1:2), yielding 428 mg (1.1 mmol, 74%) of 2-[3-(4-fluorophenyl)-propylsulfanyl]-N-(thiophen-2-yl-methyl) -pyridine-3-carboxylic acid amide. MS: m/z 3871 [M+H]+.

Workup

  1. stirringstirring
  2. waitwas carried out for a further 16 h at RT
  3. concentrationThe mixture was then concentrated in vacuo
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was extracted again with EA
  6. dry with materialThe combined organic phases were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by means of CC (EA/hex 1:2)

Sources & evidence

ORD record
ord-09b10c23eef74cf2878b5b934d9427f0
Source dataset
uspto-grants-2012_05
Patent number
US08178684B2

Reaction notes

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