Potassium Carbonate → HCID 57607467, compound

HRID 1473949Notes

Reaction equation

HRID 1473949 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[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=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]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:6]([NH2:5])[N:7]=2)[CH:10]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 251966512,2,2-trifluoro-N-(6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)acetamide2×

Product 1

HCID 57607467HCID 57607467, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

2,2,2-trifluoro-N-(6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-yl)acetamide (compound k, 0.190 g, 0.0006 mol) was dissolved in methanol (8.0 mL) and water (2 ml). To this was added potassium carbonate (0.2 g, 0.002 mol). The reaction was heated in the microwave at 100° C. for 45 min. The solvent concentrated and residue was partitioned between water (100 mL) and ethyl acetate (100 mL). The layers were separated and the organic layer was dried (magnesium sulfate) then chromatographed on silica (55:40:5, DCM:acetonitrile:MeOH) to give 6-fluoro-3-phenylimidazo[1,2-a]pyridin-2-amine Rf 0.40, (55:40:5, DCM:acetonitrle:MeOH); MS ink 228 (M+H).

Workup

  1. concentrationThe solvent concentrated
  2. customresidue was partitioned between water (100 mL) and ethyl acetate (100 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:acetonitrile:MeOH)

Sources & evidence

ORD record
ord-405f6cda49f74f44b0558319861fb627
Source dataset
uspto-grants-2015_04
Patent number
US09018208B2

Reaction notes

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