Ethyl Bromide → HCID 58208009, compound

HRID 1958496Notes

Reaction equation

HRID 1958496 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([OH:12])[C:6]2[N:7]([CH:9]=[CH:10][N:11]=2)[CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:19](Br)[CH3:20].CCOC(C)=O.CCCCCCC>CC(C)=O.CN(C=O)C>[Br:2][C:3]1[CH:4]=[C:5]([O:12][CH2:19][CH3:20])[C:6]2[N:7]([CH:9]=[CH:10][N:11]=2)[CH:8]=1

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 21899848Ethylacetate heptaneHCID 670075396-broMo-8-hydroxy-iMidazo[1,2-a] pyridine hydrochloride

Product 1

HCID 58208009HCID 58208009, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

6-Bromoimidazo[1,2-a]pyridin-8-ol hydrochloride (40 mg, 0.16 mmol) and Cs2CO3 (104 mg, 0.32 mmol) in acetone (0.64 mL) and DMF (0.2 mL) was added ethyl bromide (12 μL). The reaction was stirred for 48 h then the volatile solvents were removed and the residue then added water (0.8 mL). The resulting solids were stirred, filtered, and rinsed with water. The water filtrate was extracted with EtOAc and then combined with the solid crude products. The residue was purified via column chromatography (25% then 50% EtOAc/heptane) to afford the product (19 mg, 50% yield).

Workup

  1. customthe volatile solvents were removed
  2. stirringThe resulting solids were stirred
  3. filtrationfiltered
  4. washrinsed with water
  5. extractionThe water filtrate was extracted with EtOAc
  6. customThe residue was purified via column chromatography (25%

Sources & evidence

ORD record
ord-0671a4b5f8784dc49cdbfbab7f045087
Source dataset
uspto-grants-2013_04
Patent number
US08410128B2

Reaction notes

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