Water → HCID 178439461、化合物

HRID 1896435ノート

反応式

HRID 1896435 の反応式
F[C:2]1[CH:3]=C2[C:8](=[CH:9][CH:10]=1)[NH:7]C=C2.[H-].[Na+].Cl[CH2:14][N:15]1[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]1=[O:23].[OH2:24].C[N:26]([CH:28]=O)[CH3:27]>>[O-:24][N+:26]1[CH:28]=[CH:3][CH:2]=[C:10]2[C:9]([CH2:14][N:15]3[CH2:19][CH:18]([CH2:20][CH2:21][CH3:22])[CH2:17][C:16]3=[O:23])=[CH:8][NH:7][C:27]=12

参加物

6

反応物 5

HCID 962WaterHCID 6228Dimethylformamide2 回HCID 24758Sodium hydrideHCID 678615-FluoroindoleHCID 536292161-(Chloromethyl)-4-propylpyrrolidin-2-one

生成物 1

HCID 178439461HCID 178439461、化合物収率 33%

実験手順

To a solution of 5-fluoroindole x157 (405 mg, 3 mmol, 1 eq) of in DMF (7 ml) maintained under argon is added NaH (60% in mineral oil; 120 mg, 3 mmol, 1 eq). The resulting mixture is stirred for three hours at room temperature, then a solution of 1-(chloromethyl)-4-propylpyrrolidin-2-one x63 in DMF (1 M, 3 ml, 3 mmol, 1 eq) is added. The reaction mixture is stirred for 20 hours at room temperature. Water (70 ml) is added and the resulting mixture is extracted with ethyl acetate (30 ml). The organic phase is washed twice with water and dried over Na2SO4. After filtration and evaporation of volatiles, the crude product is purified by two consecutive chromatographs on silicagel (CH2Cl2/MeOH gradient, then CH2Cl2). Pure 1-[(7-oxido-1H-pyrrolo[2,3-b]pyridin-3-yl)methyl]-4-propylpyrrolidin-2-one 278 is obtained as syrup (274 mg).

後処理

  1. stirringThe reaction mixture is stirred for 20 hours at room temperature
  2. extractionthe resulting mixture is extracted with ethyl acetate (30 ml)
  3. washThe organic phase is washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationAfter filtration and evaporation of volatiles
  6. customthe crude product is purified by two consecutive chromatographs on silicagel (CH2Cl2/MeOH gradient

出典と根拠

ORDレコード
ord-bb69da8f00d041439c7d4d56b49b757b
出典データセット
uspto-grants-2013_08
特許番号
US08518943B2

反応ノート

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