Sodium Sulfate → HCID 57537473, compound

HRID 1693703Notes

Reaction equation

HRID 1693703 reaction equation
[Br:1][C:2]1[C:3]([CH3:19])=[C:4]2[CH:10]=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1.[I:20]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCCl.O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH3:19])=[C:4]2[C:10]([I:20])=[CH:9][N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]2=[N:6][CH:7]=1

Participants

8

Reactant 4

HCID 24436Sodium SulfateHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 57537631HCID 57537631, compound

Product 1

HCID 57537473HCID 57537473, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.439 mmol) was dissolved in anhydrous 1,2 dichloroethane (6 mL), and N-iodosuccinimide (198 mg, 0.879 mmol) was added. The solution was stirred at 23° C. for 15 hours when ethyl acetate was added. A solution of water (25 mL) and aqueous saturated sodium bicarbonate (25 mL) was added. Layers were mixed well. The organic layer was stirred over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified by flash silica gel chromatography by using a gradient of ethyl acetate in hexanes to afford 5-Bromo-3-iodo-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (80 mg, 0.171 mmol, 39%) as a white soft solid. 8.39 (s, 1H), 7.93 (s, 1H), 5.54 (s, 2H), 3.47 (t, 2H), 2.85 (s, 3H), 0.79 (s, 2H), −0.11 (s, 8H); MS [MH+] m/z: 466.9, 468.9

Workup

  1. additionwas added
  2. additionLayers were mixed well
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-06968925895c4adc9cb8fa1e228d07c9
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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