Trifluoroacetic acid → 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one

HRID 1896350ノート

反応式

HRID 1896350 の反応式
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.C(O)(C(F)(F)F)=O.O[CH2:18][N:19]1[CH2:23][CH:22]([CH2:24][CH2:25][CH3:26])[CH2:21][C:20]1=[O:27]>>[CH2:24]([CH:22]1[CH2:23][N:19]([CH2:18][C:3]2[C:4]3[C:5](=[N:6][CH:7]=[CH:8][CH:9]=3)[NH:1][CH:2]=2)[C:20](=[O:27])[CH2:21]1)[CH2:25][CH3:26]

参加物

4

反応物 3

HCID 6422Trifluoroacetic acidHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-one

生成物 1

HCID 577430754-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one収率 13%

反応条件

温度
70 °C

実験手順

To a solution of commercially available 1H-pyrrolo[2,3-b]pyridine x7 (20.31 mmol, 1.2 eq, 3.19 g) dissolved TFA (25 ml) is added 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (16.93 mmol, 1 eq, 2 g). The mixture is heated at 70° C. overnight. The solvent is then evaporated under reduce pressure. CH2Cl2 (600 ml) is then added to the residue, and the resulting organic solution is washed with a saturated aqueous solution of sodium carbonate (200 ml). The organic phase is then dried over MgSO4 and the volatiles are removed under reduced pressure. The product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v)) and recristallized in acetonitrile. 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)pyrrolidin-2-one 231 is obtained as a white solid.

後処理

  1. customThe solvent is then evaporated
  2. additionCH2Cl2 (600 ml) is then added to the residue
  3. washthe resulting organic solution is washed with a saturated aqueous solution of sodium carbonate (200 ml)
  4. dry with materialThe organic phase is then dried over MgSO4
  5. customthe volatiles are removed under reduced pressure
  6. customThe product is purified by chromatography on silicagel (CH2Cl2/MeOH/NH4OH: 97/3/0.3 (v/v/v))

出典と根拠

ORDレコード
ord-63fe9b9371f8428f99f6aaaaf213a3e9
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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