Sodium Iodide → 3-[2-(Imidazo[1,2-a]pyridin-5-yl)ethyl]thiazolidine-2,4-dione

HRID 357013Notes

Reaction equation

O[CH2:2][CH2:3][C:4]1[N:9]2[CH:10]=[CH:11][N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.S(Cl)(Cl)=O.[Na].[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].[I-].[Na+]>C(Cl)(Cl)Cl.CN(C)C=O.O>[N:12]1[CH:11]=[CH:10][N:9]2[C:4]([CH2:3][CH2:2][N:20]3[C:21](=[O:23])[CH2:22][S:18][C:19]3=[O:24])=[CH:5][CH:6]=[CH:7][C:8]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 4.0 g (24.7 mmol) of 5-(2-hydroxyethyl)imidazo[1,2-a]pyridine in 30 ml of chloroform, 5 ml (68 mmol) of thionyl chloride was added. After refluxing for 2 hours, the solvent was distilled off. To a suspension of the residue and 8.36 g (60 mmol) of 2,4-thiazolidinedione sodium salt in 50 ml of N,N-dimethylformamide, 3.75 g (25 mmol) of sodium iodide was added, followed by stirring at 80° C. for 16 hours. After the reaction mixture was cooled, water was added. The reaction mixture was then extracted with ethyl acetate and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/1→1/4) to yield 1.00 g (15.5%, light orange powder) of the desired product.

Workup

additionwas added
temperatureAfter refluxing for 2 hours
distillationthe solvent was distilled off
additionwas added
temperatureAfter the reaction mixture was cooled
extractionThe reaction mixture was then extracted with ethyl acetate
customdried
distillationafter which the solvent was distilled off
customThe residue was purified by column chromatography (eluent: n-hexane/ethyl acetate=2/1→1/1→1/4)

Sources & evidence

ORD record: ord-8022d0eff17842dc9617562550dc138d
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05840732

Reaction notes

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