Dimethyl Sulfoxide → 1H-Pyrazolo[3,4-C]pyridine-5-carboxaldehyde

HRID 218473Notes

Reaction equation

HRID 218473 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[N:2]1.CS(C)=O.CCN(CC)CC>C(Cl)Cl>[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH:10]=[O:11])[CH:9]=[C:4]2[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 59763243(1H-pyrazolo[3,4-c]pyridin-5-yl)methanol

Product 1

HCID 596944711H-Pyrazolo[3,4-C]pyridine-5-carboxaldehydeYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1H-pyrazolo[3,4-c]pyridine-5-methanol (1.08 g, 7.27 mmol) was dissolved in DCM (120 mL) at rt, and DMSO (30 mL) and NEt3 (3.01 mL, 21.7 mmol) were added. After stirring for 10 min, SO3-pyridine (3.45 g, 13.45 mmol) was added. The mixture stirred at rt for ca. 1.5 hr, and quenched with sat. NH4Cl solution. The reaction mixture was extracted with DCM, washed with water and with brine, and dried with Na2SO4. The crude product was purified by a flash column to afford 1H-pyrazolo[3,4-c]pyridine-5-carboxaldehyde (220 mg, 21%).

Workup

  1. stirringThe mixture stirred at rt for ca. 1.5 hr
  2. customquenched with sat. NH4Cl solution
  3. extractionThe reaction mixture was extracted with DCM
  4. washwashed with water and with brine
  5. dry with materialdried with Na2SO4
  6. customThe crude product was purified by a flash column

Sources & evidence

ORD record
ord-aa23225b739e48c789af53168fac7857
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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