Methyl iodide → HCID 69879819, compound

HRID 1007245Notes

Reaction equation

HRID 1007245 reaction equation
[F:1][CH:2]([F:24])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([N:17]=[C:18]=[S:19])=[C:5]([C:20]([F:23])([F:22])[F:21])[N:4]=1.[CH3:25][O-:26].[Na+].[CH3:28]I>C1COCC1.CO>[F:24][CH:2]([F:1])[C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:6]([N:17]=[C:18]([O:26][CH3:25])[S:19][CH3:28])=[C:5]([C:20]([F:23])([F:22])[F:21])[N:4]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 22668807HCID 22668807, compound

Product 1

HCID 69879819HCID 69879819, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.5 g (6.8 mmol) of methyl 2-(difluoromethyl)-5-isothiocyanato-4-(2-methylpropyl)-6-(trifluoromethyl)-3-pyridinecarboxylate (U.S. Pat. No. 5,129,943 example 41 step A) in 25 ml of anhydrous THF at room temperature was added 1.6 g (7.5 mmol) of 25% sodium methoxide in methanol. The reaction mixture was stirred for 30 min and was treated with 1.93 g (14 mmol) of methyl iodide. The reaction mixture was stirred for 3 h and concentrated in vacuo. The residue was partitioned with ether (75 ml) and 10% HCl (50 ml). The organic layer was washed with water (3×30 ml), dried (MgSO4), and concentrated in vacuo. The crude product was purified by chromatotron (20% EtOAc in hexane) to afford 2.32 g (82%) of a colorless oil, n25D 1.5982.

Workup

  1. stirringThe reaction mixture was stirred for 3 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned with ether (75 ml) and 10% HCl (50 ml)
  4. washThe organic layer was washed with water (3×30 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by chromatotron (20% EtOAc in hexane)

Sources & evidence

ORD record
ord-1092a07d26c048809610333a13624827
Source dataset
uspto-grants-2004_09
Patent number
US06794396B2

Reaction notes

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