Water → 3-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

HRID 253406Notes

Reaction equation

HRID 253406 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[CH:13]([Si:16](Cl)([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])([CH3:15])[CH3:14].O>CN(C)C=O>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([Si:16]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:13]([CH3:15])[CH3:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 53770783-Iodo-7-azaindole

Product 1

HCID 242292273-Iodo-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridineYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Iodo-1H-pyrrolo[2,3-b]pyridine 67 (2.00 g, 8.20 mmol) was dissolved in N,N-dimethylformamide (50 mL). Sodium hydride (60% dispersion in mineral oil, 390 mg, 9.8 mmol) was added. After 20 minutes, triisopropylsilyl chloride (1.74 mL, 8.20 mmol) was added dropwise. After 1.5 hours, the reaction was poured into water and extracted with ethyl acetate, washed with saturated sodium bicarbonate and brine. The organic portions were dried over anhydrous sodium sulfate and concentrated. Purification by silica gel chromatography, 0-25% gradient ethyl acetate/hexane gave compound 68 as a white solid (3.224 g, 98.2%). 1H-NMR was consistent with the desired compound.

Workup

  1. waitAfter 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate and brine
  4. dry with materialThe organic portions were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography, 0-25% gradient ethyl acetate/hexane

Sources & evidence

ORD record
ord-50f8963d1b7e4be28e243488ca376921
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

Loading…