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

HRID 1625253Notes

Reaction equation

HRID 1625253 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-a7f2e08ab2194607aba0abdc260f5bee
Source dataset
uspto-grants-2014_07
Patent number
US08779142B2

Reaction notes

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