Ethyl Acetate → HCID 67500364, compound

HRID 1625260Notes

Reaction equation

HRID 1625260 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([C:11]([F:14])([F:13])[F:12])[C:3]=12.C(=O)([O-])[O-:16].[Cs+].[Cs+].[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1F)[C:25]#[N:26].C(OCC)(=O)C>C(#N)C>[Cl:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:29]=1[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([I:1])=[C:3]2[C:10]([C:11]([F:14])([F:12])[F:13])=[N:9]1)[C:25]([NH2:26])=[O:16]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1455253-Chloro-4-fluorobenzonitrileHCID 178506295HCID 178506295, compound

Product 1

HCID 67500364HCID 67500364, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Compound (153a) (5.0 g), cesium carbonate (7.82 g), and 3-chloro-4-fluorobenzonitrile (3.0 g) were suspended in acetonitrile (50 mL), followed by stirring at 70° C. for 24 hr. The reaction solution was distributed between ethyl acetate and an aqueous ammonium chloride solution, and the organic layer was washed with saturated saline. The organic layer after the washing was dried over anhydrous sodium sulfate, and then the solvent was distilled away. Ethanol was added to the residue, and the precipitate was collected by filtration to obtain 3-chloro-4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide (4.77 g, 66%). 3-Chloro-4-{4-iodo-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl}benzamide (2.53 g) was dissolved in DMSO (28 mL). A hydrogen peroxide solution (30 wt %) (0.700 mL) and a 4 mol % aqueous sodium hydroxide solution (1.41 mL) were added to the resulting solution, followed by stirring at room temperature for 20 min. Water was added to the reaction solution, and the precipitate was collected by filtration and was dried under reduced pressure to obtain compound (153b) (2.26 g, 86%).

Workup

  1. washan aqueous ammonium chloride solution, and the organic layer was washed with saturated saline
  2. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled away
  4. additionEthanol was added to the residue
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-548d536e00ff41f8a7d8b44b7b63b02f
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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