Sodium Iodide → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-iodo-pyridin-3-yl]-N-methyl-isobutyramide

HRID 1835336Notes

Reaction equation

HRID 1835336 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21](Cl)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[I-:36].[Na+].I.C(=O)(O)[O-].[Na+]>CC(C)C(=O)C.COC(C)(C)C>[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([C:13]([CH3:33])([CH3:32])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([I:36])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24841Hydrogen iodideHCID 516892Sodium BicarbonateHCID 23502837HCID 23502837, compound

Product 1

HCID 235027902-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(2-chloro-phenyl)-6-iodo-pyridin-3-yl]-N-methyl-isobutyramideYield 74.5%

Reagents, catalysts & solvents 2

HCID 112513-Methyl-2-butanoneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 250 mg (0.467 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[6-chloro-4-(2-chloro-phenyl)-pyridin-3-yl]-N-methyl-isobutyramide (Example 24), 250 mg (1.64 mmol) sodium iodide and 0.12 ml (0.99 mmol) hydroiodic acid (57% in water) in 5 ml 3-methyl-2-butanone was heated at 80° C. for 5 h in a sealed tube. After cooling to room temperature the mixture was diluted with tert-butyl methyl ether and treated with saturated aqueous sodium bicarbonate solution. The layers were separated, the organic layer washed with water, dried with magnesium sulfate and concentrated. Flash column chromatography gave 218 mg (48%) of the title compound as a light brown solid.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customThe layers were separated
  3. washthe organic layer washed with water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c5355b8f5d7b41669845b20bd01e1cd2
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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