Pyrrolidine → 3-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(pyrrolidin-1-yl)-5-(trifluoromethyl)picolinic acid

HRID 887863Notes

Reaction equation

HRID 887863 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[C:5]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1>[CH3:17][C:12]1[N:11]([C:5]2[C:6]([C:8]([OH:10])=[O:9])=[N:7][C:2]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[C:3]([C:18]([F:21])([F:20])[F:19])[CH:4]=2)[C:15]([CH3:16])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 866576686-Bromo-3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)picolinic acid

Product 1

HCID 584423303-(2,5-Dimethyl-1H-pyrrol-1-yl)-6-(pyrrolidin-1-yl)-5-(trifluoromethyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 6-bromo-3-(2,5-dimethyl-1H-pyrrol-1-yl)-5-(trifluoromethyl)picolinic acid (300 mg, 0.826 mmol) in THF (1 ml), pyrrolidine (0.136 ml, 1.652 mmol) was added. The orange solution was stirred at RT overnight. The reaction mixture was partitioned between 0.5M HCl (30 ml) and EtOAc (30 ml) and shaken. The organic portion was separated and washed with brine (30 ml), dried over MgSO4, filtered and concentrated in vacuo to give a red oil. The crude product was purified on silica eluting with 0-40% EtOAc in iso-hexane to afford the title product;

Workup

  1. customThe reaction mixture was partitioned between 0.5M HCl (30 ml) and EtOAc (30 ml)
  2. stirringshaken
  3. customThe organic portion was separated
  4. washwashed with brine (30 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a red oil
  9. customThe crude product was purified on silica eluting with 0-40% EtOAc in iso-hexane

Sources & evidence

ORD record
ord-d1e9a5761f2a45a49340da85eee0342d
Source dataset
uspto-grants-2012_08
Patent number
US08247436B2

Reaction notes

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