Dimethylformamide → 3-(2-Pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

HRID 2265981Notes

Reaction equation

HRID 2265981 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=1.CN(C=O)C.[NH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>CCOC(C)=O>[N:22]1([C:2]2[C:7]([CH:8]=[CH:9][C:10]([OH:12])=[O:11])=[CH:6][CH:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[N:3]=2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 723356323-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687840033-(2-Pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acidYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (100 mg, 0.397 mmol) in pyrrolidine (1.0 ml) was added DMF (1.0 ml). The mixture was stirred for 12 hours at room temperature. The reaction mixture was diluted with EtOAc and then washed two times with 1N-HCl and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was column-chromatographed to yield the 3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (100 mg, 91%).

Workup

  1. washwashed two times with 1N-HCl and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was column-chromatographed

Sources & evidence

ORD record
ord-a836f511f6704d19b0ca9823af6d9f76
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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