Potassium Carbonate → HCID 18466902, compound

HRID 2229192Notes

Reaction equation

HRID 2229192 reaction equation
Br[CH:2]([CH2:10][C:11]1[CH:16]=[C:15]([Br:17])[CH:14]=[CH:13][C:12]=1[O:18][CH3:19])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:20]OC1C=CC(Br)=CC=1CCC(OCC)=O.[NH2:36][C:37]1[CH:42]=N[CH:40]=[CH:39][N:38]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:17][C:15]1[CH:14]=[CH:13][C:12]([O:18][CH3:19])=[C:11]([CH2:10][C:2]2[N:38]3[CH:39]=[CH:40][CH:20]=[CH:42][C:37]3=[N:36][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:16]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 78747AminopyrazineHCID 18466882Ethyl 3-(5-bromo-2-methoxyphenyl)propanoateHCID 18466885HCID 18466885, compound

Product 1

HCID 18466902HCID 18466902, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 11.94 g of the 3:2 mixture of ethyl 3-bromo-4-(2-methoxy-5-bromophenyl)-2-oxobutanoate and ethyl 3-(2-methoxy-5-bromophenyl)propanoate in 150 mL of ethanol is treated with 2.85 g (30.0 mmol) of 2-aminopyrazine and heated to reflux temperature for 16 hr. The reaction mixture is cooled to room temperature and treated with 10 g of potassium carbonate. The mixture is filtered through Celite and the solvent removed in vacuo to yield the crude material. The resulting residue is flash chromatographed with initially 1% methanol in dichloromethane and then 3% methanol in dichloromethane to afford 3.7 g (48% based on starting material) ethyl 3-[(5-bromo-2-methoxyphenyl)methyl]-imidazolo[1,2-a]pyridine-2-carboxylate.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 16 hr
  3. filtrationThe mixture is filtered through Celite
  4. customthe solvent removed in vacuo
  5. customto yield the crude material
  6. customchromatographed with initially 1% methanol in dichloromethane

Sources & evidence

ORD record
ord-a8562f0234f247d583a5e75531bb70ca
Source dataset
uspto-grants-2002_07
Patent number
US06420365B1

Reaction notes

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