3-(Chloromethyl)pyridine hydrochloride → HCID 59389378, compound

HRID 2357936Notes

Reaction equation

HRID 2357936 reaction equation
[CH2:1]([C:3]1[CH:20]=[C:6]2[C:7]([C:12]3[CH:13]([CH3:19])[CH2:14][C:15](=[O:18])[NH:16][N:17]=3)=[CH:8][C:9]([F:11])=[CH:10][N:5]2[N:4]=1)[CH3:2].[H-].[Na+].Cl.Cl[CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>CN(C=O)C>[CH2:1]([C:3]1[CH:20]=[C:6]2[C:7]([C:12]3[CH:13]([CH3:19])[CH2:14][C:15](=[O:18])[N:16]([CH2:25][C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)[N:17]=3)=[CH:8][C:9]([F:11])=[CH:10][N:5]2[N:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 24758Sodium hydrideHCID 59389325HCID 59389325, compound

Product 1

HCID 59389378HCID 59389378, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 199 (100 mg) was dissolved in DMF (3.6 mL) and 60% sodium hydride (32 mg) was added at 0° C. The mixture was stirred at room temperature for 30 min. Subsequently, 3-(chloromethyl)pyridine-hydrochloride (65.8 mg) was added and the mixture was stirred at 60° C. for 6 hours. The reaction was terminated by adding a saturated aqueous ammonium chloride solution and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. Evaporation of the solvent under reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=1:4) afforded the title compound as a yellow powder (98.5 mg).

Workup

  1. stirringthe mixture was stirred at 60° C. for 6 hours
  2. customThe reaction was terminated
  3. additionby adding a saturated aqueous ammonium chloride solution
  4. extractionthe mixture was extracted three times with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation of the solvent
  8. customunder reduced pressure and purification by silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-36b426263ad24cb2b9b995c7f320a192
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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