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

HRID 660059ノート

反応式

HRID 660059 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-107a00e5d1014a2d85e5395f9e05ba4b
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

反応ノート

読み込み中…