Water → HCID 66727774, compound

HRID 573335

Reaction equation

HRID 573335 reaction equation
[CH3:1][S:2][C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=1.Br[CH2:13][CH2:14][O:15][CH3:16].O>CN(C=O)C>[CH3:16][O:15][CH2:14][CH2:13][N:11]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[N:4]=[C:3]1[S:2][CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 809722-Bromoethyl methyl etherHCID 178503348HCID 178503348, compound

Product 1

HCID 66727774HCID 66727774, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(methylthio)-3H-imidazo[4,5-b]pyridine (400 mg) and 1-bromo-2-methoxyethane (370 mg) in DMF (7 mL) was stirred at 80° C. for 3 h, treated with water, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (200 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-121940b42852495aba1fb74a162ccf8a
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Linked notes

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