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

HRID 2288474Notes

Reaction equation

HRID 2288474 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. Yield: 0.33 g (67% of theory) of yellow amorphous solid, Rf value: 0.52 (silica gel; ethyl acetate/petroleum ether=1:4)

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-e98327d2b5f940c1b2cd6ec64f69eeae
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

Loading…