Potassium Carbonate → HCID 18182188, compound

HRID 1359389Notes

Reaction equation

HRID 1359389 reaction equation
[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([SH:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][CH2:18][CH2:19][CH2:20]CS([O-])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][CH:11]=[C:10]([S:15][CH2:20][CH2:19][CH2:18][O:17][CH3:16])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59513339HCID 59513339, compoundHCID 178527716HCID 178527716, compound

Product 1

HCID 18182188HCID 18182188, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 500 mg of 2-benzyl-3-bromo-6-mercaptopyridine, 360 mg of 3-methoxypropylmethane sulfonate, 370 mg of anhydrous potassium carbonate and 10 ml of N,N-dimethylformamide was stirred at room temperature for one hour in a nitrogen atmosphere. The reaction solution was partitioned between ethyl acetate-water, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography using 1-2% ethyl acetate/hexane, to give 425 mg of the target compound.

Workup

  1. customThe reaction solution was partitioned between ethyl acetate-water
  2. washthe organic phase was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1fd81987c58148d2980e952e76a19976
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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