Iodine → HCID 178488170, compound

HRID 2182391Notes

Reaction equation

HRID 2182391 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2.[I:12]I.[OH-].[K+].S(=O)(O)[O-].[Na+]>CN(C)C=O>[I:12][C:6]1[C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[NH:8][N:7]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 133468605-Methoxy-1H-indazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 178488170HCID 178488170, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-methoxy-1H-indazole [0.815 g, Reference Example 24(a)] in dimethyl formamide (8 ml) was treated with iodine (2.80 g) and potassium hydroxide (1.16 g). The mixture was stirred at ambient temperature for 1 hour then poured into 10% aqueous sodium bisulfite solution (200 ml) and then extracted three times with ethyl acetate. The combined organic extracts were washed with water, then with brine, then dried over magnesium sulfate and then evaporated to yield 3-iodo-5-methoxy-1H-indazole (1.48 g) as a yellow solid. LC-MS (METHOD B): RT=2.96 minutes; 275 (M+H)+. (b) 4-Fluoro-3-iodo-1H-indazole

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic extracts were washed with water
  3. dry with materialwith brine, then dried over magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-01fd710afe3c43d591bffc10814225e3
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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