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

HRID 80244

Reaction equation

HRID 80244 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-486874dd47bb489285c1af4af84829f7
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

Loading…