Iodine → HCID 178526460, compound

HRID 1671281Notes

Reaction equation

HRID 1671281 reaction equation
[I:1]I.[OH-].[K+].[N+:5]([C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[N:13][NH:14]2)=[CH:10][CH:9]=1)([O-:7])=[O:6].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C)C=O>[I:1][C:12]1[C:11]2[C:15](=[CH:16][C:8]([N+:5]([O-:7])=[O:6])=[CH:9][CH:10]=2)[NH:14][N:13]=1

Participants

6

Reactant 4

HCID 807IodineHCID 14797Potassium HydroxideHCID 242396-NitroindazoleHCID 24477Sodium Thiosulfate

Product 1

HCID 178526460HCID 178526460, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodine (2.14 g, manufactured by Kanto Chemical Co., Inc.) and potassium hydroxide (475 mg, manufactured by Wako Pure Chemical Industries, Ltd.) were added to a solution of 6-nitro-1H-indazole (690 mg, manufactured by Wako Pure Chemical Industries, Ltd.) in N,N-dimethylformamide (20 mL, manufactured by Kanto Chemical Co., Inc.), and the mixture was stirred for one hour at room temperature. A saturated aqueous solution of sodium thiosulfate (20 mL) was added to the reaction solution, and the mixture was extracted with chloroform (3×20 mL), washed with brine (40 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=9:1), to give 1.04 g of the title compound. LC-MS: HPLC retention time 0.54 minutes, m/z 290 (M+H), condition C-3.

Workup

  1. extractionthe mixture was extracted with chloroform (3×20 mL)
  2. washwashed with brine (40 mL)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was then evaporated
  5. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-8315ed848fcd45e8808ede473e834eef
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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