Iodine → HCID 178488170, compound

HRID 2064645Notes

Reaction equation

HRID 2064645 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)+.

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-5b33eaaa63b046afaa57aa068b7fc685
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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