Methyl iodide → HCID 9929871, compound

HRID 2293468Notes

Reaction equation

HRID 2293468 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:13][C:12](=[O:14])[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:4][CH:3]=1.[C:27]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([O:14][CH3:27])[C:11]([C:15]#[N:16])=[CH:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:21][CH:22]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15408575HCID 15408575, compound

Product 1

HCID 9929871HCID 9929871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.34 g (0.92 mMol) of 1,2-dihydro-6-(4-fluorophenyl)-5-[4-(methylthio)phenyl]-2-oxo-pyridine-3-carbonitrile (Step 3) in 10 ml of DMF and 0.33 g of K2CO3 and 2 ml of iodomethane, was stirred at room temperature over the weekend. The reaction mixture was diluted with 75 ml of water and extracted with dichloromethane (4×25 ml). The combined organic layers were extracted once with 50 ml of 10% NaOH solution then once with brine, dried over MgSO4 and evaporated to dryness. The residue was purified by HPLC to give two fractions. The first fraction was the desired product: m.p. 202.5°-204° C.

Workup

  1. extractionextracted with dichloromethane (4×25 ml)
  2. extractionThe combined organic layers were extracted once with 50 ml of 10% NaOH solution
  3. dry with materialonce with brine, dried over MgSO4
  4. customevaporated to dryness
  5. customThe residue was purified by HPLC
  6. customto give two fractions

Sources & evidence

ORD record
ord-9d5eee2e08824b27b3cb5bc2099980a7
Source dataset
uspto-grants-1997_11
Patent number
US05686470

Reaction notes

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