Iodine → HCID 178506575, compound

HRID 1157414Notes

Reaction equation

HRID 1157414 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[I:10]I.[OH-].[K+]>CN(C=O)C.OS([O-])=O.[Na+]>[I:10][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:1][N:2]=1

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 27558501H-pyrazolo(3,4-b)pyridine

Product 1

HCID 178506575HCID 178506575, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

A solution of 1.00 g (8.40 mmol) of 1H-pyrazolo[3,4-b]pyridine in 15 mL of DMF was treated with 4.26 g (16.80 mmol) of iodine, followed by 1.77 g (31.50 mmol) of solid KOH. The resulting reddish-brown mixture was stirred at ambient temperature for 1 hour. The reaction was diluted with 5× its volume with a solution of aq. 10% NaHSO3, and the mixture stirred. The yellow solid precipitate was filtered off, washed with water, and dried in vacuo to give the desired product. The crude product was used as is in the next reaction. MS M+1=246.

Workup

  1. stirringthe mixture stirred
  2. filtrationThe yellow solid precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2e9802405c5e4cdbb3d2f8212406d229
Source dataset
uspto-grants-2010_10
Patent number
US07807684B2

Reaction notes

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