Potassium Carbonate → 6-Fluoro-3-methylimidazo[1,2-a]pyridin-2-amine

HRID 1971634Notes

Reaction equation

FC(F)(F)C([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[CH3:16])=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:14][C:11]1[CH:12]=[CH:13][C:8]2[N:9]([C:15]([CH3:16])=[C:6]([NH2:5])[N:7]=2)[CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

2,2,2-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)acetamide (0.188 g, 0.00072 mol) was dissolved in methanol (4.0 mL) and water (0.5 mL). Potassium carbonate (0.40 g, 0.0029 mol) was added and heated in the microwave for 45 min at 100° C. The solvent concentrated and residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated and the organic layer was dried (magnesium sulfate) then chromatographed on silica (55:40:5, DCM:acetonitrle:MeOH) to give 6-fluoro-3-methylimidazo[1,2-a]pyridin-2-amine Rf 0.47, (55:40:5, DCM:acetonitrle:MeOH); MS m/z 166 (M+H).

Workup

concentrationThe solvent concentrated
customresidue was partitioned between water (50 mL) and ethyl acetate (50 mL)
customThe layers were separated
dry with materialthe organic layer was dried (magnesium sulfate)
customthen chromatographed on silica (55:40:5, DCM:acetonitrle:MeOH)

Sources & evidence

ORD record: ord-2a58be0708f443308d5504e2e42851ab
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431608B2

Reaction notes

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