Trifluoroacetic acid → N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide

HRID 537029Notes

Reaction equation

HRID 537029 reaction equation
COC1C=C(OC)C=CC=1C[N:6]([C:12]1[CH:17]=[C:16]([I:18])[C:15]([CH3:19])=[CH:14][N:13]=1)[C:7]([CH:9]1[CH2:11][CH2:10]1)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[I:18][C:16]1[C:15]([CH3:19])=[CH:14][N:13]=[C:12]([NH:6][C:7]([CH:9]2[CH2:11][CH2:10]2)=[O:8])[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66747562N-(2,4-dimethoxybenzyl)-N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide

Product 1

HCID 66748424N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamideYield 83.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(2,4-dimethoxybenzyl)-N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide (1.8 g, 3.95 mmol) in DCM (23 mL) was added TFA. The reaction mixture was allowed to stir at rt overnight and then concentrated. The residue was diluted with DCM and aqueous saturated NaHCO3 and the mixture was extracted with DCM. The organic solutions were combined, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give N-(4-iodo-5-methylpyridin-2-yl)cyclopropanecarboxamide (1.0 g, 75%).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with DCM and aqueous saturated NaHCO3
  3. extractionthe mixture was extracted with DCM
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3e12a041bb0b4cafa7c1ecfc038fe888
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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