Iodine → HCID 178432860, compound

HRID 590772Notes

Reaction equation

HRID 590772 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[CH:9]=[N:10][NH:11][C:4]=2[CH:3]=1.[OH-].[K+].[I:14]I.S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOC(C)=O.CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]2[C:9]([I:14])=[N:10][NH:11][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 807Iodine2×HCID 14797Potassium Hydroxide2×HCID 24477Sodium ThiosulfateHCID 1181689536-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 178432860HCID 178432860, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

A 100 mL round bottom flask was charged with 6-chloro-4-methyl-1H-pyrazolo[4,3-c]pyridine (1.20 g, 7.16 mmol) and DMF (28.5 mL). The reaction flask was warmed to 70° C. and KOH (1.2 g, 21.48 mmol) was added. Iodine (5.45 g, 21.48 mmol) was added gradually over 1 h. The reaction mixture was stirred for 3 h then additional KOH (3.2 g, 57.0 mmol) and iodine (15.6 g, 61.5 mmol) were added. The reaction was heated at 70° C. for 2 h. The reaction was poured into saturated sodium thiosulfate (500 mL) and diluted with EtOAc (200 mL). The aqueous phase was extracted with EtOAc (200 mL, ×2). The combined organic phase was washed with water (200 mL) and brine (200 mL), dried over MgSO4, filtered, and concentrated in vacuo to give 6-chloro-3-iodo-4-methyl-1H-pyrazolo[4,3-c]pyridine. MS ESI calc'd. for C7H5ClIN3 [M+1]+ 294. found 294.

Workup

  1. temperatureThe reaction was heated at 70° C. for 2 h
  2. extractionThe aqueous phase was extracted with EtOAc (200 mL, ×2)
  3. washThe combined organic phase was washed with water (200 mL) and brine (200 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52138570570f42b6a974ec41e1586acc
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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