Iodine → HCID 178506572, compound

HRID 1774952Notes

Reaction equation

HRID 1774952 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[CH:15]=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:2]=1.[OH-].[K+].[I:18]I>CN(C=O)C>[I:18][C:15]1[C:9]2[C:10](=[CH:11][N:12]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:8]=2)[NH:13][N:14]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 866766805-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 178506572HCID 178506572, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine (196 g, 1 mol) was dissolved in 1000 mL DMF. KOH (112 g, 2 mol) was added. After stirring for 30 min, I2 (303 g, 1.2 mol) was added. The mixture was stirred for 1 h at room temperature. After reaction, the reaction was quenched with saturated aq. Na2S2O5 solution followed by the addition water (5 L). The solid was filtered and washed with water to give 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine as a yellow solid (290 g, 90%)

Workup

  1. stirringThe mixture was stirred for 1 h at room temperature
  2. customAfter reaction
  3. customthe reaction was quenched with saturated aq. Na2S2O5 solution
  4. additionfollowed by the addition water (5 L)
  5. filtrationThe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-823187ec546d44e9b922ffba1fd7348d
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

Loading…