Ethyl Acetate → HCID 18446614, compound

HRID 1269082Notes

Reaction equation

HRID 1269082 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([C:17](=[O:19])[CH3:18])=[N:10][N:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=23)[CH:5]=[CH:4][N:3]=1.[Br:20]Br.C(OCC)(=O)C>C(O)(=O)C>[Br:20][CH2:18][C:17]([C:9]1[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([F:1])[CH:7]=2)=[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]2[N:10]=1)=[O:19]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24408BromineHCID 18446593HCID 18446593, compound

Product 1

HCID 18446614HCID 18446614, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1-[3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-2-yl]ethanone (580 mg, 2.27 mmol) in acetic acid (20 mL) was added bromine (0.12 mL, 2.27 mmol). After heating at 80° C. for 30 minutes, the solution was cooled to room temperature. Ethyl acetate was added to dilute the reaction mixture. The mixture was washed with water (×3), brine and dried over magnesium sulfate. Filtration and concentration, followed by recrystallization from ethyl acetate gave 2-bromo-1-[3-(2-fluoro-4-pyridinyl)pyrazolo[1,5-a]pyridin-2-yl]ethanone (478 mg, 64%) as a yellow solid. 1H NMR (CDCl3): δ 8.51 (d, 1H), 8.27 (d, 1H), 7.65 (d, 1H), 7.33 (m, 2H), 7.10 (s, 1H), 7.06 (t, 1H), 4.76 (s, 2H). MS m/334 (M+1).

Workup

  1. temperaturethe solution was cooled to room temperature
  2. additionto dilute the reaction mixture
  3. washThe mixture was washed with water (×3), brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration
  6. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-594c3d7f98aa42cb9fa732cf16f652ae
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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