1,2-Dimethoxyethane → Methyl 3-(4-methoxyphenyl)imidazo[1,2-a]pyridine-6-carboxylate

HRID 452597Notes

Reaction equation

HRID 452597 reaction equation
I[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+].COCCOC>C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:6]3[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 16413170Methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 68663056Methyl 3-(4-methoxyphenyl)imidazo[1,2-a]pyridine-6-carboxylateYield 56%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate (1.40 g, 4.63 mmol), (4-methoxyphenyl)boronic acid (845 mg, 5.56 mmol), tetrakis(triphenylphosphine)palladium(0) (268 mg, 0.232 mmol), 2 M aqueous sodium carbonate solution (4.63 mL) and 1,2-dimethoxyethane (50 mL) was heated under reflux under an argon atmosphere overnight. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-0/1) to give the title compound (730 mg, yield 56%) as colorless crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under an argon atmosphere overnight
  3. temperatureAfter cooling
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/1-0/1)

Sources & evidence

ORD record
ord-e491777344e74e37ab78977e9cfe666a
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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