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

HRID 1473962Notes

Reaction equation

HRID 1473962 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

5

Reactant 2

HCID 11430Potassium CarbonateHCID 576074742,2,2-trifluoro-N-(6-fluoro-3-methylimidazo[1,2-a]pyridin-2-yl)acetamide

Product 1

HCID 576074616-Fluoro-3-methylimidazo[1,2-a]pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

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

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

Sources & evidence

ORD record
ord-e5f6b5e57c004d96b537fbfa0755dfe3
Source dataset
uspto-grants-2015_04
Patent number
US09018208B2

Reaction notes

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