1-(Hydroxymethyl)-4-propylpyrrolidin-2-one → 1-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1924248Notes

Reaction equation

HRID 1924248 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.O[CH2:12][N:13]1[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]1=[O:21]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]2=[N:8][N:9]([CH2:12][N:13]3[CH2:17][CH:16]([CH2:18][CH2:19][CH3:20])[CH2:15][C:14]3=[O:21])[CH:10]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 404274545-Bromopyrazolo[3,4-b]pyridine

Product 1

HCID 577430451-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-oneYield 7.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine x80 (1 g, 1 eq, 5.04 mmol) and 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (1.58 g, 2 eq, 10.08 mmol) in trifluoroacetic acid (20 ml) is refluxed for 4 hours. The reaction mixture is poured on crushed ice, on saturated NaHCO3 aqueous solution, and the aqueous phase is extracted with dichloromethane. The cumulated organic layers are dried over MgSO4, filtered, evaporated under reduced pressure. The crude product is purified by preparative chromatography on silicagel affording 1-[(5-bromo-2H-pyrazolo[3,4-b]pyridin-2-yl)methyl]-4-propylpyrrolidin-2-one 291 as a white solid.

Workup

  1. additionThe reaction mixture is poured
  2. customon crushed ice
  3. extractionon saturated NaHCO3 aqueous solution, and the aqueous phase is extracted with dichloromethane
  4. dry with materialThe cumulated organic layers are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe crude product is purified by preparative chromatography

Sources & evidence

ORD record
ord-60d25e7877224c01af19d0bc77e85a57
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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