Dimethylformamide → 2-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]-3-iodopyridine

HRID 1359343Notes

Reaction equation

HRID 1359343 reaction equation
[I:1]N1C(=O)CCC1=O.CN(C)C=O.[CH2:14]([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([N:27]2[CH2:31][C@@H:30]([F:32])[C@H:29]([F:33])[CH2:28]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>O>[CH2:14]([C:21]1[C:26]([I:1])=[CH:25][CH:24]=[C:23]([N:27]2[CH2:28][C@@H:29]([F:33])[C@H:30]([F:32])[CH2:31]2)[N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120273N-IodosuccinimideHCID 697594382-Benzyl-6-[(3r,4r)-3,4-difluoropyrrolidine-1-yl]pyridine

Product 1

HCID 697590462-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]-3-iodopyridineYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

94 mg of N-iodosuccinic acid imide was added little by little to 5.0 ml of an N,N-dimethylformamide solution containing 104 mg of 2-benzyl-6-[(3R,4R)-3,4-difluoropyrrolidine-1-yl]pyridine under ice-cooling, followed by stirring overnight as it was. Water was added to the reaction solution and the mixture was extracted with ethyl acetate. The organic phase was washed with an aqueous sodium thiosulfate solution, water and brine, and the solvent was removed. The residue was subjected to NH-silica gel (Fuji Silicia) column chromatography and eluted with hexane/ethyl acetate (10:1), to give 152 mg of the target compound.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic phase was washed with an aqueous sodium thiosulfate solution, water and brine
  4. customthe solvent was removed
  5. washeluted with hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-d1a8f7464bda4a56a5fdd641b333ee2a
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

Loading…