Iodine → HCID 178455023, compound

HRID 245951Notes

Reaction equation

HRID 245951 reaction equation
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].[I:18]I.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][N:11]=[C:10]2[I:18])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 11430Potassium CarbonateHCID 580425115-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1H-indazole

Product 1

HCID 178455023HCID 178455023, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round-bottomed flask, 5-(tert-butyl-dimethyl-silanyloxy)-1H-indazole (1.20 g, 4.83 mmol) was dissolved in DMF (12 ml). Iodine (2.45 g, 9.66 mmol) was added followed by potassium carbonate (2.58 g, 18.7 mmol). The dark suspension was stirred at room temperature for 3 h then quenched with 10% aqueous NaHSO3 and extracted with diethyl ether (2×). The combined organic layers were washed with 10% aqueous NaHSO3, three times with water and once with brine then dried over sodium sulfate, filtered and concentrated to afford 1.65 g (91%) of 5-(tert-butyl-dimethyl-silanyloxy)-3-iodo-1H-indazole as a dark brown foam.

Workup

  1. customthen quenched with 10% aqueous NaHSO3
  2. extractionextracted with diethyl ether (2×)
  3. washThe combined organic layers were washed with 10% aqueous NaHSO3, three times with water and once with brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab11783009c84a739eb510414586ec03
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…