Water → 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)pyrrolidin-2-one

HRID 1896470Notes

Reaction equation

HRID 1896470 reaction equation
[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[CH:17][N:16]([Si](C(C)C)(C(C)C)C(C)C)[C:13]3=[N:14][CH:15]=2)[C:6](=[O:29])[CH2:5]1)[CH2:2][CH3:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.O>C1COCC1>[CH2:1]([CH:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:11]=[C:12]3[CH:18]=[CH:17][NH:16][C:13]3=[N:14][CH:15]=2)[C:6](=[O:29])[CH2:5]1)[CH2:2][CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 2724141Tetrabutylammonium FluorideHCID 536292094-propyl-1-{[1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}pyrrolidin-2-one

Product 1

HCID 577430874-propyl-1-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)pyrrolidin-2-oneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-propyl-1-{[1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]methyl}pyrrolidin-2-one x256 (0.7 g, 1.7 mmol) is dissolved in absolute THF (7 ml). A 1 M solution of tetrabutylammonium fluoride in THF (1.7 M, 1 eq) is added. The obtained solution is stirred for 10 min at room temperature and poured into a mixture of ether (100 ml) and water (20 ml). The organic phase is separated, dried with anhydrous sodium sulfate, and evaporated. The residue is purified by chromatography on silicagel (dichloromethane/isopropanol) to yield 0.43 g of 4-propyl-1-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)pyrrolidin-2-one 241.

Workup

  1. customThe organic phase is separated
  2. dry with materialdried with anhydrous sodium sulfate
  3. customevaporated
  4. customThe residue is purified by chromatography on silicagel (dichloromethane/isopropanol)

Sources & evidence

ORD record
ord-3890cdae0bea4e13846c40b19a0cc5ac
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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