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

HRID 80251Notes

Reaction equation

HRID 80251 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.Cl[CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([CH2:12][O:13][CH2:14][CH2:15][Si:16]([CH3:19])([CH3:18])[CH3:17])[C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 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 64.2%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-bromo-1H-pyrrolo[2,3-b]pyridine (0.3 g, 1.6 mmol) was reacted with (2-chloromethoxy-ethyl)-trimethyl-silane (0.35 g, 2.1 mmol), catalytic amount of benzyl triethyl-ammonium chloride and NaOH (0.2 g, 5.2 mmol) and DCM (20 mL) to afford the crude product. Purification by column chromatography on silica gel (20% ethylacetate in hexane) afforded 0.32 g of the product (64.2% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (20% ethylacetate in hexane)

Sources & evidence

ORD record
ord-dacbc8ac76544d36b0b2b7399ac6d0d0
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Reaction notes

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