Iodine → HCID 178422879, compound

HRID 922467Notes

Reaction equation

HRID 922467 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[NH:8][N:9]=[CH:10][C:5]2=[CH:4][CH:3]=1.[I:11]I.[OH-].[K+]>CN(C)C=O>[I:11][C:10]1[C:5]2[C:6](=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[NH:8][N:9]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 552533026-Methyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178422879HCID 178422879, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-methyl-1H-pyrazolo[3,4-b]pyridine (4.44 g) and iodine (16.9 g) in N,N-dimethylformamide (100 mL) was added potassium hydroxide (7.48 g) under ice-cooling, and the mixture was stirred at room temperature for 4 hours. The reaction solution was poured into ice water, and the precipitate was filtered. The filtrate was extracted with ethyl acetate, washed with saturated saline, and then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was combined with the above-mentioned precipitate and purified by silica gel column chromatography (eluent: chloroform→chloroform/methanol=19/1) to give 3-iodo-6-methyl-1H-pyrazolo[3,4-b]pyridine [REx(104-2)] (6.48 g) as a brown powder.

Workup

  1. temperaturecooling
  2. filtrationthe precipitate was filtered
  3. extractionThe filtrate was extracted with ethyl acetate
  4. washwashed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel column chromatography (eluent: chloroform→chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-ca5bb403b39e4f6dbcafd9e807ab5f77
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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