Chloroform → 3-Formyl-4-{4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrile

HRID 921565Notes

Reaction equation

HRID 921565 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([CH:11]([CH3:13])[CH3:12])[C:3]=12.C(=O)([O-])[O-].[Cs+].[Cs+].F[C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][C:22]=1[CH:29]=[O:30].C(Cl)(Cl)Cl>C(#N)C.O>[CH:29]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][C:21]=1[N:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([I:1])=[C:3]2[C:10]([CH:11]([CH3:13])[CH3:12])=[N:9]1)[C:25]#[N:26])=[O:30]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 10796Cesium carbonateHCID 109097255-Cyano-2-fluorobenzaldehydeHCID 178440425HCID 178440425, compound

Product 1

HCID 866646033-Formyl-4-{4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl}benzonitrileYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound (100a) (2.0 g), cesium carbonate (3.41 g), and 4-fluoro-3-formylbenzonitrile (1.25 g) were suspended in acetonitrile (23 mL), followed by reflux for 3 hr. The reaction solution was distributed between chloroform and water, 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. The residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (125a) (2.00 g, 67%) as a white solid.

Workup

  1. temperatureby reflux for 3 hr
  2. washthe organic layer was washed with saturated saline
  3. dry with materialThe organic layer after the washing was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away
  5. customThe residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-97f13c0c626f46e5af04f5de5e8c6309
Source dataset
uspto-grants-2016_03
Patent number
US09273045B2

Reaction notes

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