Sodium Iodide → HCID 67409087, compound

HRID 1949654Notes

Reaction equation

HRID 1949654 reaction equation
[Na+].[I-].[F:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH:23]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:22][CH:21]1[CH:33]=[CH:34][N+:35]([O-:37])=[O:36])=[O:19])([CH3:16])([CH3:15])[CH3:14]>CO.CC#N>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH:23]([O:25][Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27])[CH2:22][CH:21]1[CH:33]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([F:3])=[CH:5][CH:6]=2)[NH:10][CH:9]=1)[CH2:34][N+:35]([O-:37])=[O:36])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 3512786-FluoroindoleHCID 67212929HCID 67212929, compound

Product 1

HCID 67409087HCID 67409087, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of CeCl3.7H2O (6.06 g, 40.6 mmol) and NaI (2.44 g, 16.2 mmol) in MeOH (200 mL) was added SiO2 (30 g). The resulting pale yellow solution was evaporated to dryness to afford a fine yellow powder. To this solid was added 6-fluoroindole (6.59 g, 48.7 mmol) and a solution of 77 (15.1 g, 40.6 mmol) in anhydrous CH3CN (150 mL). The heterogeneous reaction mixture was evaporated to dryness and allowed to stand 72 h at ambient temperature. The reaction mixture was diluted with CH2Cl2 and additional silica gel (150 mL) was added. The mixture was concentrated to dryness and the product was eluted by flash silica gel chromatography (15-25% EtOAc/hexanes) to afford 78 (15.3 g, 75%) as an inseparable mixture of diastereomers. Mass spectrum, m/z [508.2] (M+H)+.

Workup

  1. customThe resulting pale yellow solution was evaporated to dryness
  2. customto afford a fine yellow powder
  3. customThe heterogeneous reaction mixture was evaporated to dryness
  4. additionThe reaction mixture was diluted with CH2Cl2 and additional silica gel (150 mL)
  5. additionwas added
  6. concentrationThe mixture was concentrated to dryness
  7. washthe product was eluted by flash silica gel chromatography (15-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca26dbc03d1a4bbdbc6099f5c032f78c
Source dataset
uspto-grants-2013_03
Patent number
US08399683B2

Reaction notes

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