Lawesson's reagent → Methyl 2-methoxymethyl-thiazolo[5,4-b]pyridine-6-carboxylate

HRID 992640Notes

Reaction equation

HRID 992640 reaction equation
Cl[C:2]1[C:11]([NH:12][C:13](=O)[CH2:14][O:15][CH3:16])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:27])=CC=1>C1(C)C(C)=CC=CC=1>[CH3:16][O:15][CH2:14][C:13]1[S:27][C:2]2[C:11]([N:12]=1)=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=2

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 18412377Methyl 6-chloro-5-methoxyacetamidonicotinate

Product 1

HCID 18412416Methyl 2-methoxymethyl-thiazolo[5,4-b]pyridine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 0.53 g (2.05 mMol) of methyl 6-chloro-5-methoxyacetamido-nicotinate and 0.42 g (1.0 mMol) of Lawessons reagent was refluxed for 16 hours in 25 ml of xylene. After the solvent had been removed in vacuo the crude product obtained was purified by flash chromatography (silica gel; methylene chloride/ethanol=100:1) and evaporated down again in vacuo.

Workup

  1. customAfter the solvent had been removed in vacuo the crude product
  2. customobtained
  3. customwas purified by flash chromatography (silica gel; methylene chloride/ethanol=100:1)
  4. customevaporated down again in vacuo

Sources & evidence

ORD record
ord-697c8aa0e7a542bcaac8669a66f7de05
Source dataset
uspto-grants-2002_10
Patent number
US06469039B1

Reaction notes

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