Triacetoxyperiodinane → HCID 13732607, compound

HRID 1499099Notes

Reaction equation

HRID 1499099 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:3]=12.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:3]=12

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 20209064(4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)methanol

Product 1

HCID 13732607HCID 13732607, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

(4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridin-5-yl)-methanol SAO 33034 (359 mg, 1.70 mmol) was dissolved in anhydrous CH2Cl2 (50 mL) at RT under nitrogen. Dess Martin Periodinane (755 mg, 1.78 mmol) was slowly added portionwise at 4° C. The reaction mixture was stirred for 1 h at 4° C. then overnight at RT. The solid was filtered off and CH2Cl2 (200 mL) was added to the mixture. After separation, the organic layer was washed with brine (20 mL), dried over MgSO4, filtered and evaporated to give 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbaldehyde SAO 33058 (see table 5) as an off-white solid (711 mg, 100%).

Workup

  1. customovernight
  2. customat RT
  3. filtrationThe solid was filtered off
  4. additionCH2Cl2 (200 mL) was added to the mixture
  5. customAfter separation
  6. washthe organic layer was washed with brine (20 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-85a82701117d4105b26c7b68592896be
Source dataset
uspto-grants-2015_12
Patent number
US09200016B2

Reaction notes

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