Iodine → HCID 178526495, compound

HRID 227729Notes

Reaction equation

HRID 227729 reaction equation
[I:1]I.[OH-].[K+].[N+:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2)([O-:7])=[O:6]>CN(C=O)C>[I:1][C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=2)[NH:13][N:12]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 215015-Nitroindazole

Product 1

HCID 178526495HCID 178526495, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodine (1.6 g, 6.4 mmol) and KOH (0.67 g, 12 mmol) were successfully added into a solution of 5-nitro-1H-indazole (520 mg, 3.2 mmol) in DMF. The reaction mixture was stirred at room temperature for overnight and then 10% Na2S2O5 was poured into the mixture. The titled compound (0.84 g, 91%) was filtered off as a yellow solid. MS (ESI) m/z=290 [M+H]+. 1H NMR (400 MHz, d6-DMSO) δ 14.15(s, 1H), 8.36(d, J=2 Hz, 1H), 8.26 (dd, J=2 and 9 Hz, 1H), 7.78 (d, J=9 Hz, 1H)

Workup

  1. filtrationThe titled compound (0.84 g, 91%) was filtered off as a yellow solid

Sources & evidence

ORD record
ord-a8618b138c4f4b9d917aad6a66e980f6
Source dataset
uspto-grants-2009_07
Patent number
US07560467B2

Reaction notes

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