Potassium Carbonate → HCID 69447259, compound

HRID 1373790Notes

Reaction equation

HRID 1373790 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+]>C(N)CCC>[CH2:6]([NH:7][C:2]1[N:7]2[N:8]=[C:9]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[C:10]([C:11](=[O:13])[CH3:12])=[C:6]2[CH:5]=[CH:4][CH:3]=1)[CH2:5][CH2:4][CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 223500461-(7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)ethanone

Product 1

HCID 69447259HCID 69447259, compoundYield 166.5%

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

A mixture of 1-[7-chloro-2-(4-fluorophenyl)pyrazolo[1,5-α]pyridin-3-yl]ethanone (969 mg, 3.4 mmol) and potassium carbonate (9.6 g, 69.4 mmol) in n-butylamine (20 mL) was heated to reflux for 5 hours. The mixture was cooled to room temperature and concentrated in vacuo. The residue was taken up in ethyl acetate and water. The organic layer was washed with brine. The aqueous layer was extracted with ethyl acetate and the combined organics were dried over sodium sulfate. Filtration and concentration followed by flash chromatography (2:1 hexanes-ethyl acetate) provided 1-[7-(butylamino)-2-(4-fluorophenyl)pyrazolo[1 ,5-α]pyridin-3-yl]ethanone (921 mg, 84%) as a tinted oil. 1H NMR (CDCl3): δ 7.71 (d, 1H), 7.63 (dd, 2H), 7.49 (t, 1H), 7.23 (t, 2H), 6.16 (d, 1H), 6.10 (m, 1H), 3.40 (m, 2H), 2.18 (s, 3H), 1.78 (m, 2H), 1.52 (m, 2H), 1.02 (t, 3H); MS m/z 326 (M+1); Rf 0.6 (1:1 hexanes:ethyl acetate).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 5 hours
  3. concentrationconcentrated in vacuo
  4. washThe organic layer was washed with brine
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. dry with materialthe combined organics were dried over sodium sulfate
  7. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-9aa356f9fce24be2ace58b74350da413
Source dataset
uspto-grants-2007_01
Patent number
US07163940B2

Reaction notes

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