Iodine → HCID 178452221, compound

HRID 1292997Notes

Reaction equation

HRID 1292997 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([CH:18]=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+].[I:25]I>CN(C)C=O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:22]=[C:21]3[C:17]([C:18]([I:25])=[N:19][NH:20]3)=[CH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 44242925tert-Butyl 4-(1H-indazol-6-yl)piperazine-1-carboxylate

Product 1

HCID 178452221HCID 178452221, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A stirred solution of 6-[4-(t-butoxycarbonyl)piperazin-1-yl]-1H-indazole (7.20 g, 23.8 mmol) in N,N-dimethylformamide at 0° C. is treated with powdered potassium hydroxide (5.40 g, 95.4 mmol) followed by the dropwise addition of a solution of iodine (10.9 g, 42.9 mmol) in N,N-dimethylformamide, stirred at ambient temperatures for 16 h, diluted with ethyl acetate and quenched with 10% aqueous sodium metabisulfite solution. The phases are separated. The aqueous phase is extracted with ethyl acetate. The extracts are combined with the organic phase, washed with brine, dried over sodium sulfate and concentrated in vacuo. The resulting crude material is purified by flash chromatography (silica gel, 30:70 ethyl acetate/hexanes) to afford the title compound as a yellow solid, 3.4 g (38% yield) identified by NMR and mass spectral analyses.

Workup

  1. customquenched with 10% aqueous sodium metabisulfite solution
  2. customThe phases are separated
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude material is purified by flash chromatography (silica gel, 30:70 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a733eaea74db4604ba979f084a0bb0cc
Source dataset
uspto-grants-2007_07
Patent number
US07238696B2

Reaction notes

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