Methanol → HCID 66598454, compound

HRID 334567Notes

Reaction equation

HRID 334567 reaction equation
Br[C:2]1[N:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].CO.[C:23]1(B(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1(C)C=CC=CC=1.O.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>[C:23]1([C:2]2[N:7]3[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 19701375Ethyl 5-bromoimidazo[1,2-a]pyridine-2-carboxylate

Product 1

HCID 66598454HCID 66598454, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of ethyl 5-bromo-imidazo[1,2-a]pyridine-2-carboxylate (1.50 g, 5.6 mmol), Pd(PPh3)4 (322 mg, 0.279 mmol) in a mixture of toluene (17 mL), NaHCO3 1M (6 mL) and MeOH (4 mL) was added phenylboronic acid at room temperature. The resulting reaction mixture was heated at 80° C. for 12 h, cooled, and diluted with water (50 mL). The insoluble matter was filtered off, and the phases were separated. The aqueous phase was extracted with ethyl acetate, the combined organic layers were washed with water and the solvent was removed under reduced pressure. The crude product was purified by chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent) to afford 1.41 g of ethyl 5-phenyl-imidazo[1,2-a]pyridine-2-carboxylate (Yield: 95%) as a yellowish solid (M.P.: 123-123.8° C.)

Workup

  1. customThe resulting reaction mixture
  2. temperaturecooled
  3. filtrationThe insoluble matter was filtered off
  4. customthe phases were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic layers were washed with water
  7. customthe solvent was removed under reduced pressure
  8. customThe crude product was purified by chromatography (prepacked 25 g silicagel column, DCM/MeOH from 100/0 to 99/1 as eluent)

Sources & evidence

ORD record
ord-03f87ddc833b422b95b162990158a75e
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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