Iodine → HCID 66778502, compound

HRID 1035477Notes

Reaction equation

HRID 1035477 reaction equation
[I:1]I.[CH3:3][N:4]1[CH:8]=[C:7]([C:9]2[CH:10]=[C:11]3[CH:17]=[CH:16][NH:15][C:12]3=[N:13][CH:14]=2)[CH:6]=[N:5]1.[OH-].[K+].S([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[I:1][C:17]1[C:11]2[C:12](=[N:13][CH:14]=[C:9]([C:7]3[CH:6]=[N:5][N:4]([CH3:3])[CH:8]=3)[CH:10]=2)[NH:15][CH:16]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 24437Sodium SulfiteHCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridine

Product 1

HCID 66778502HCID 66778502, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

8.2 A solution of 1.125 g (4.4 mmol) of iodine in 16 ml of DMF is slowly added dropwise at RT to a suspension of 901 mg (4.4 mmol) of 5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine and 620 mg (11.1 mmol) of KOH in 12 ml of DMF. When the addition is complete, the mixture is stirred at RT for a further 30 min. The reaction mixture is subsequently poured into 300 ml of an ice-cold, saturated sodium sulfite solution. The yellow precipitate is filtered off with suction and washed with 10 ml of ice-cold water. The filter residue is dried, giving 3-iodo-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine as beige crystals, ESI 325

Workup

  1. additionWhen the addition
  2. filtrationThe yellow precipitate is filtered off with suction
  3. washwashed with 10 ml of ice-cold water
  4. customThe filter residue is dried

Sources & evidence

ORD record
ord-a3d33ce300134f59bed061d5bad8e891
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

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