Trifluoroacetic acid → HCID 178461565, compound

HRID 1625527Notes

Reaction equation

HRID 1625527 reaction equation
[I:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([C@@H:9]3[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10]3C(OC(C)(C)C)=O)=[N:8][C:4]=2[CH:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[I:1][C:2]1[CH:23]=[CH:22][C:5]2[NH:6][C:7]([C@@H:9]3[CH2:13][C@H:12]([CH3:14])[CH2:11][NH:10]3)=[N:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178461441HCID 178461441, compound

Product 1

HCID 178461565HCID 178461565, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of tert-butyl (2S,4S)-2-(5-iodo-1H-benzimidazol-2-yl)-4-methyl-pyrrolidine-1-carboxylate (3.70 g, 8.659 mmol) in dichloromethane (34 mL) is added TFA (17.22 mL, 223.5 mmol) and stirred at rt for 1 h. The reaction mixture is concentrated, azeotroped 2× with toluene and dried in vacuo. The residue is diluted with dichloromethane (200 mL), washed 2× with saturated sodium bicarbonate and brine and then dried over sodium sulfate. The organic is evaporated to give 5-iodo-2-[(2S,4S)-4-methylpyrrolidin-2-yl]-1H-benzimidazole (2.32 g, 82%).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customazeotroped 2× with toluene
  3. customdried in vacuo
  4. additionThe residue is diluted with dichloromethane (200 mL)
  5. washwashed 2× with saturated sodium bicarbonate and brine
  6. dry with materialdried over sodium sulfate
  7. customThe organic is evaporated

Sources & evidence

ORD record
ord-b9c8e18637f84e899e36010de8a79163
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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