N,N-Dimethylglycine → N-[(2S)-5-(2-pyridinyloxy)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide

HRID 1922301ノート

反応式

HRID 1922301 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)CC(O)=O>CS(C)=O.[Cu]I>[N:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C@H:6]([NH:11][S:12]([CH:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[CH2:5]2

参加物

7

反応物 4

HCID 673N,N-DimethylglycineHCID 79732-BromopyridineHCID 10796Cesium carbonateHCID 66857149(S)-N-(5-hydroxy-2,3-dihydro-1H-inden-2-yl)propane-2-sulfonamide

生成物 1

HCID 44124720N-[(2S)-5-(2-pyridinyloxy)-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide収率 32.4%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
190 °C

実験手順

A reaction mixture of N-[(2S)-5-hydroxy-2,3-dihydro-1H-inden-2-yl]-2-propanesulfonamide (100 mg, 0.39 mmol, Description 3), 2-bromopyridine (62 mg, 0.39 mmol), caesium carbonate (382 mg, 1.17 mmol), copper(I) iodide (82 mg, 0.43 mmol) and N,N-dimethylglycine (49 mg, 0.47 mmol) in DMSO (1.5 ml) was heated in a microwave at 190° C. for 30 minutes. The resulting mixture was then partitioned between dichloromethane and water and the organic solution was dried (MgSO4) and evaporated under reduced pressure to yield the crude product. The crude product was purified using MDAP. The resulting solution was diluted with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic solution was dried (MgSO4) and evaporated under reduced pressure to obtain the title compound as a yellow gum (42 mg).

後処理

  1. customThe resulting mixture was then partitioned between dichloromethane and water
  2. dry with materialthe organic solution was dried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto yield the crude product
  5. customThe crude product was purified
  6. additionThe resulting solution was diluted with saturated aqueous sodium bicarbonate solution
  7. extractionextracted with dichloromethane
  8. dry with materialThe organic solution was dried (MgSO4)
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-b3067db738094521aab945ce0fb4d209
出典データセット
uspto-grants-2012_05
特許番号
US08173820B2

反応ノート

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