Iodine → HCID 59238645, compound

HRID 1924480Notes

Reaction equation

HRID 1924480 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]3[CH:12]=[C:13]4[CH:19]=[CH:18][NH:17][C:14]4=[N:15][CH:16]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[OH-].[K+].[I:22]I>CN(C=O)C>[I:22][C:19]1[C:13]2[C:14](=[N:15][CH:16]=[C:11]([CH:8]3[CH2:7][CH2:6][C:5]4([O:4][CH2:3][CH2:2][O:1]4)[CH2:10][CH2:9]3)[CH:12]=2)[NH:17][CH:18]=1

Participants

5

Reactant 3

HCID 807IodineHCID 14797Potassium HydroxideHCID 59238626HCID 59238626, compound

Product 1

HCID 59238645HCID 59238645, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the azaindole (XIb-19) (2.51 g, 9.72 mmol) in DMF (40 mL), was added crushed KOH pellets (2.05 g, 36.6 mmol) followed by I2 (2.22 g, 8.7 mmol). The mixture was stirred at room temperature for 3.5 h and concentrated in vacuum. The residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 solution (40 mL). The aqueous layer was extracted with EtOAc (3×60 mL). The combined organic solutions were dried (MgSO4), filtered and concentrated. The residue consisting of crude iodide (XIIb-19) was used for the preparation of (IXb-19) without any additional purification.

Workup

  1. concentrationconcentrated in vacuum
  2. customThe residue was partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 solution (40 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×60 mL)
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customwas used for the preparation of (IXb-19) without any additional purification

Sources & evidence

ORD record
ord-bcaf6062aaf14e828f286fee589fa231
Source dataset
uspto-grants-2012_05
Patent number
US08178552B2

Reaction notes

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