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

HRID 50335Notes

Reaction equation

HRID 50335 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-methoxyacetamidonicotinate and 0.42 g (1.0 mmol) of Lawesson's 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

Sources & evidence

ORD record
ord-59bb81b45d4943e9a0e2915c274e8193
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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