Water → 6-Bromo-2-isopropylcarbonyl-imidazo[1,2-a]pyridine

HRID 601679

Reaction equation

HRID 601679 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13]CC)=O)[N:10]=2)[CH:7]=1.[CH:16]([Mg]Cl)([CH3:18])[CH3:17].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([CH:16]([CH3:18])[CH3:17])=[O:13])[N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7141939Ethyl 6-bromoimidazo[1,2-a]pyridine-2-carboxylateHCID 178418918HCID 178418918, compound

Product 1

HCID 231582326-Bromo-2-isopropylcarbonyl-imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

269 mg of 6-bromo-2-ethoxycarbonyl-imidazo[1,2-a]pyridine obtained in Example 117 was dissolved in 10 ml of tetrahydrofuran, cooled down to −78° C., and 0.5 ml of 2M isopropylmagnesium chloride was dropped thereto. After heating to −40° C., water was added and the products were extracted with ethyl acetate. Organic layer was dried with anhydrous magnesium sulfate, and the solvents were distilled outunder reduced pressure. The obtained residues were purified by silicagel column chromatography (hexane:ethyl acetate=50:50) to obtain 58.5 mg of the above compound.

Workup

  1. temperatureAfter heating to −40° C.
  2. extractionthe products were extracted with ethyl acetate
  3. dry with materialOrganic layer was dried with anhydrous magnesium sulfate
  4. distillationthe solvents were distilled outunder reduced pressure
  5. customThe obtained residues were purified by silicagel column chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record
ord-776bf12ee64a4cb5bfe4174d875ec94b
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Linked notes

Loading…