Sodium Iodide → HCID 68469185, compound

HRID 506773Notes

Reaction equation

HRID 506773 reaction equation
[Na+].[I-:2].Cl[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:7]1>CC(=O)CC>[I:2][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[N:10][C:11]([O:17][CH3:18])=[C:12]([O:15][CH3:16])[CH:13]=2)[C:8]([C:19]2[N:27]([S:28]([C:31]3[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=3)(=[O:30])=[O:29])[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[CH:20]=2)=[CH:7]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 68472349HCID 68472349, compound

Product 1

HCID 68469185HCID 68469185, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Add NaI (1.10 equiv., 30 mg, 0.20 mmol) to bisazaindole 17 (93 mg, 0.182 mmol) in 2-butanone (10 mL). After 16 h of reflux, the reaction mixture is concentrated under vacuum and the residue is dissolved in EtOAc (100 mL), washed with brine, dried (MgSO4) and concentrated, to give 18 (105 mg, 91%) as an ivory-colored solid: TLC (EtOAc at 40%/heptane) Rf=0.08, m/z obs.=604 (M+1).

Workup

  1. temperatureAfter 16 h of reflux
  2. concentrationthe reaction mixture is concentrated under vacuum
  3. dissolutionthe residue is dissolved in EtOAc (100 mL)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0bc303afcff2439db25dc6c49c6f7a2e
Source dataset
uspto-grants-2010_08
Patent number
US07786114B2

Reaction notes

Loading…