Water → 2,2,2-trifluoro-N-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)acetamide

HRID 1473960Notes

Reaction equation

[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]2[CH:15]=1)=[O:4].[I:18]N1C(=O)CCC1=O.O>C(#N)C>[F:17][C:2]([F:16])([F:1])[C:3]([NH:5][C:6]1[N:7]=[C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][N:9]2[C:15]=1[I:18])=[O:4]

Participants

Conditions

Temperature: 0 °C

Procedure

2,2,2-trifluoro-N-(6-fluoroimidazo[1,2-a]pyridin-2-yl)acetamide (0.89 g, 0.0036 mol) was dissolved in acetonitrile (20 mL) and was cooled at 0° C. N-Iodosuccinimide (0.89 g, 0.0040 mol) was added and the reaction was stirred for 30 minutes. The mixture was poured into water (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organics were dried with magnesium sulfate and the solvent removed. The residue was chromatographed on silica (60% ethyl acetate/hexanes) to give 2,2,2-trifluoro-N-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)acetamide 4 Rf 0.40, 60% ethyl acetate/hexanes; MS m/z 374 (M+H).

Workup

extractionextracted with ethyl acetate (3×100 mL)
dry with materialThe combined organics were dried with magnesium sulfate
customthe solvent removed
customThe residue was chromatographed on silica (60% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-3e20c40b5615468fa14ace26950f54dd
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018208B2

Reaction notes

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