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

HRID 2043573Notes

Reaction equation

HRID 2043573 reaction equation
[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]

Participants

4

Reactant 3

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

Product 1

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

Conditions

Temperature
70 °C

Procedure

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.

Workup

  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))

Sources & evidence

ORD record
ord-e9367f0e6d8948809b2043e77b7283e9
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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