HCID 21834439, compound → HCID 21834442, compound

HRID 1740973Notes

Reaction equation

HRID 1740973 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[N:13]=[C:12]([N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[CH3:20])[CH:11]=[C:10]([CH3:21])[CH:9]=1)(=O)=O.[C:22]1(=[O:32])[NH:26][C:25](=[O:27])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.[K]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:21][C:10]1[CH:9]=[C:8]([CH2:7][CH2:6][N:26]2[C:25](=[O:27])[C:24]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]3[C:22]2=[O:32])[N:13]=[C:12]([N:14]2[C:18]([CH3:19])=[CH:17][CH:16]=[C:15]2[CH3:20])[CH:11]=1

Participants

5

Reactant 2

HCID 21834439HCID 21834439, compoundHCID 24194345Phthalimide potassium salt

Product 1

HCID 21834442HCID 21834442, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of 250 mg (0.906 mmol) of 6-(2-methanesulfonyloxyethyl)-4-methyl-2-(2,5-dimethylpyrrol-1-yl)pyridine (from Example 59, Step A) in 0.70 mL of dry N,N-dimethylformide was added 336 mg (1.81 mmol) of potassium phthalimide and 67 mg (0.18 mmol) of tetrabutylammonium iodide. The mixture was stirred at room temperature for 2 h and at 40° C. for 20 h. The reaction was diluted with 50 mL of dichloromethane, washed with 30 mL of saturated aqueous sodium bicarbonate and 30 mL of saturated aqueous sodium chloride, dried (sodium sulfate), decanted, and evaporated. To remove the contaminating phthalimide, the residue was dissolved in 40 mL of diethyl ether and washed 2×20 mL of 2.5 N aqueous sodium hydroxide, followed by saturated aqueous sodium chloride. The organic phase was dried (sodium sulfate), decanted, and concentrated. Flash column chromatography on 26 g of silica gel, eluting with 200 mL of 7% of ethyl acetate/hexane and 500 mL of 30% of ethyl acetate/hexane furnished 206 mg (63% yield) of 4-methyl-2-(2,5-dimethylpyrrol-1-yl)-6-(2-phthalimidoethyl)pyridine as an amber syrup.

Workup

  1. washwashed with 30 mL of saturated aqueous sodium bicarbonate and 30 mL of saturated aqueous sodium chloride
  2. dry with materialdried (sodium sulfate)
  3. customdecanted
  4. customevaporated
  5. customTo remove the contaminating phthalimide
  6. dissolutionthe residue was dissolved in 40 mL of diethyl ether
  7. washwashed 2×20 mL of 2.5 N aqueous sodium hydroxide
  8. dry with materialThe organic phase was dried (sodium sulfate)
  9. customdecanted
  10. concentrationconcentrated
  11. washFlash column chromatography on 26 g of silica gel, eluting with 200 mL of 7% of ethyl acetate/hexane and 500 mL of 30% of ethyl acetate/hexane

Sources & evidence

ORD record
ord-05cda8c721ed4cc8ac4dda7bd5de07fe
Source dataset
uspto-grants-1999_10
Patent number
US05972975

Reaction notes

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