Potassium Iodide → Ethyl 4-[(4-isopropyl-1,3-thiazol-2-yl)methoxy]-2-pyridinecarboxylate

HRID 1828427Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=1.Cl[CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH:20]([CH3:22])[CH3:21])[N:19]=1.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:20]([C:18]1[N:19]=[C:15]([CH2:14][O:1][C:2]2[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:3]=2)[S:16][CH:17]=1)([CH3:22])[CH3:21]

Participants

Conditions

Temperature: 110 °C

Procedure

Ethyl 4-hydroxy-2-pyridinecarboxylate (19.5 g, 0.057 mol) dissolved in dimethylformamide (200 ml) was added with a solution of 2-(chloromethyl)-4-isopropyl-1,3-thiazole (11 g, 0.063 mol) in dimethylformamide (150 ml). The mixture was added with potassium iodide (9.5 g) and potassium carbonate (12 g) at room temperature, then heated to 110° C. and stirred for 1 hour. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with chloroform and washed with water. The resulting organic layer was washed with saturated brine, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (chloroform) to obtain 8.049 g (46%) of the title compound.

Workup

customwas returned to room temperature
customthe solvent was evaporated under reduced pressure
additionThe residue was diluted with chloroform
washwashed with water
washThe resulting organic layer was washed with saturated brine
dry with materialthe organic layer was dried over magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography (chloroform)

Sources & evidence

ORD record: ord-1abc6c72148649ca874c2d0ccc4b616f
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07056917B2

Reaction notes

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