Methyl iodide → 2,2,2-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)acetamide

HRID 1971633Notes

Reaction equation

[F:1][C:2]([F:18])([F:17])[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]=1I)=[O:4].[Li+].[CH3:20]CC[CH2-].CI>O1CCCC1>[F:1][C:2]([F:18])([F:17])[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[CH3:20])=[O:4]

Participants

Conditions

Temperature: -78 °C

Procedure

2,2,2-trifluoro-N-(6-fluoro-3-iodoimidazo[1,2-a]pyridin-2-yl)acetamide (0.500 g, 0.00134 mol) was dissolved in tetrahydrofuran (16 mL) and was cooled at −78° C. N-Butyllithium (2 molarin cyclohexane, 1.6 mL) was added and the reaction was warmed to −20 for 15 minutes then chilled to −78° C. Methyl iodide (110 uL, 0.0017 mol) was added and the reaction was allowed to warm to room temperature. The reaction was poured into ice water and extracted with ethyl acetate (3×50 mL). The combined organics were dried (magnesium sulfate) and solvent removed. Residue chromatographed on silica (50% ethyl acetate/hexanes) to give 2,2,2-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)acetamide 5 Rf 0.47, 50% ethyl acetate/hexanes; MS m/z 262 (M+H).

Workup

temperaturethe reaction was warmed to −20 for 15 minutes
temperaturethen chilled to −78° C
temperatureto warm to room temperature
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe combined organics were dried (magnesium sulfate) and solvent
customremoved
customResidue chromatographed on silica (50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-aebb9b8a1ef24902a6cb30571933d3f1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431608B2

Reaction notes

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