Sodium hydride → 1H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-

HRID 510201Notes

Reaction equation

HRID 510201 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH3:13][Si:14]([CH2:17][CH2:18][O:19][CH2:20]Cl)([CH3:16])[CH3:15]>CN(C=O)C.[NH4+].[Cl-]>[Br:1][C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][N:7]([CH2:20][O:19][CH2:18][CH2:17][Si:14]([CH3:16])([CH3:15])[CH3:13])[C:8]2=[N:9][CH:10]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 598250161H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-Yield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 5-bromo-7-azaindole (Aldrich, 2 g, 10.15 mmol) in DMF (40.6 ml) at 0° C. was added sodium hydride (0.690 g, 17.26 mmol). The reaction was aged for 10 min followed by addition of SEM-Cl (2.340 ml, 13.20 mmol). The reaction was allowed to warm to RT and stir for 4 h. The mixture was diluted with saturated NH4Cl (30 mL) and product extracted with ethyl acetate (30 mL). The organic extract was washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (50 g, 0-50% ethyl acetate/hexanes) to give the compound 4-1a (3.2 gm) as a clear oil.

Workup

  1. extractionextracted with ethyl acetate (30 mL)
  2. extractionThe organic extract
  3. washwas washed with brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on silica gel (50 g, 0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f37f59d9aca74442b5ba269e0a864a11
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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