Ethyl Acetate → 6-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridine

HRID 2383931Notes

Reaction equation

HRID 2383931 reaction equation
Cl[CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7].[OH-].[Na+].[Br:12][C:13]1[CH:14]=[C:15]2[N:21]=[CH:20][NH:19][C:16]2=[N:17][CH:18]=1.C(OC(=O)C)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl.CCCCCC>[Br:12][C:13]1[CH:14]=[C:15]2[N:21]=[CH:20][N:19]([CH2:2][O:3][CH2:4][CH2:5][Si:6]([CH3:9])([CH3:8])[CH3:7])[C:16]2=[N:17][CH:18]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 9115786-Bromo-4H-imidazo[4,5-b]pyridineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 193582886-Bromo-3-[[2-(trimethylsilyl)ethoxy]methyl]-3H-imidazo[4,5-b]pyridineYield 14.4%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

(2-Chloromethoxy-ethyl)-trimethyl-silane (508.6 mg, 3.0456 mmol), catalytic amount of benzyl triethyl-ammonium chloride and NaOH (203.04 mg, 5.076 mmol) were added to a solution of 6-bromo-3H-imidazo[4,5-b]pyridine (500 mg, 2.538 mmol) in DCM (10 mL) at 0° C. The resulting mixture was stirred room temperature for 6 hours. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was partitioned between DCM and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (20% ethylacetate in hexane) afforded 120 mg of the product (14.4% yield).

Workup

  1. customThe reaction mixture was partitioned between DCM and water
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by column chromatography on silica gel (20% ethylacetate in hexane)

Sources & evidence

ORD record
ord-c2f7d6b69230422db0015242029973d8
Source dataset
uspto-grants-2012_09
Patent number
US08263635B2

Reaction notes

Loading…