Iodine → HCID 178428765, compound

HRID 2241280Notes

Reaction equation

HRID 2241280 reaction equation
[Cl:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][N:15]=[CH:16][C:9]=12.[OH-].[K+].[I:24]I>CN(C=O)C>[Cl:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[CH:4][C:5]([CH3:18])=[C:6]([CH:17]=1)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]2[NH:14][N:15]=[C:16]([I:24])[C:9]=12

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 685159114-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 178428765HCID 178428765, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4-(5-chloro-2-methyl-4-nitrophenoxy)-1H-pyrazolo[3,4-b]pyridine (21.0 g, 68.9 mmol) in DMF (100 mL) was added freshly ground (mortar/pestle) potassium hydroxide (11.6 g, 207 mmol) flakes followed immediately by iodine (26.2 g, 103 mmol) under N2 at 25° C. The dark reaction was heated to 50° C. for 6 hours. The mixture was quenched by addition of aqueous 10% NaHSO3 (75 mL). The suspension was further diluted by addition of water (100 mL) and filtered. The resulting precipitate washed with water, dried by toluene azeotrope, and then left under high vacuum for 2 days. The beige powder (26.5 g, 69%) was carried forward without further purification.

Workup

  1. customThe dark reaction
  2. customThe mixture was quenched by addition of aqueous 10% NaHSO3 (75 mL)
  3. additionThe suspension was further diluted by addition of water (100 mL)
  4. filtrationfiltered
  5. washThe resulting precipitate washed with water
  6. dry with materialdried by toluene azeotrope
  7. customThe beige powder (26.5 g, 69%) was carried forward without further purification

Sources & evidence

ORD record
ord-d5a98808af69453c8cda2ae1ee41163a
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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