Methyl iodide → HCID 23036709, compound

HRID 1709751Notes

Reaction equation

HRID 1709751 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1.I[CH3:20]>CN(C)C=O>[F:3][C:4]1[CH:5]=[C:6]([N:10]([CH3:20])[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 4879626HCID 4879626, compound

Product 1

HCID 23036709HCID 23036709, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 60% sodium hydride (1.76 g, 44 mmol) in dry dimethylformamide (50 mL) under nitrogen was added dropwise a solution of N-(3-fluorophenyl)-2-pyridinecarboxamide (6.87 g, 32 mmol), prepared by the process of Example 4, Step 1, in dimethylformamide (25 mL) over 30 minutes. After 30 minutes more, iodomethane (3.58 mL, 57 mmol) was added. The reaction mixture was quenched with water (500 mL), extracted with ether (3×400 mL) and further extracted with ethyl acetate (300 mL). After washing with brine the ethyl acetate layer was combined with the other organic extracts, which were dried and preadsorbed onto silica gel. Flash chromatography (250 g of silica gel gradient elution with 20-50% ethyl acetate in petroleum ether) was utilized to afford N-(3-fluorophenyl)-N-methyl-2-pyridinecarboxamide (3.81 g, 52%) m.p. 75°-78° C.

Workup

  1. customThe reaction mixture was quenched with water (500 mL)
  2. extractionextracted with ether (3×400 mL)
  3. extractionfurther extracted with ethyl acetate (300 mL)
  4. washAfter washing with brine the ethyl acetate layer
  5. customwere dried
  6. washFlash chromatography (250 g of silica gel gradient elution with 20-50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-88a5851dfbf4475baddf7daac7692d3b
Source dataset
uspto-grants-1990_08
Patent number
US04950762

Reaction notes

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