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

HRID 556330Notes

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-ba23804fb7fc4c01a9f3c5a04ce674a2
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058274B2

Reaction notes

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