Potassium Carbonate → 1-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

HRID 82644Notes

Reaction equation

HRID 82644 reaction equation
Br[C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[N:8]=[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][N:10]3[CH:15]=2)=[CH:4][CH:3]=1.[NH:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[CH2:20][C:19]1=[O:27].CN[C@@H]1CCCC[C@H]1NC.C([O-])([O-])=O.[K+].[K+]>[Cu]I>[N:8]1[C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([N:18]3[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH2:20][C:19]3=[O:27])=[CH:3][CH:4]=2)=[CH:15][N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=12

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 138640951,3-Dihydro-2H-pyrrolo(2,3-b)pyridin-2-oneHCID 679931672-(4-Bromophenoxy)imidazo[1,2-a]pyridine

Product 1

HCID 585774991-[4-(imidazo[1,2-a]pyridin-2-yloxy)phenyl]-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-oneYield 20%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
180 °C

Procedure

Ethyl 2-chloroimidazo[1,2-a]pyridine-3-carboxylate (2.00 g) was added to a solution of p-bromophenol (1.617 g) and NaH (0.427 g) in DMF(dry) (10 ml) at 100° C. The mixture was stirred at 100° C. under a dry atmosphere overnight. The reaction mixture was diluted with MeOH, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, eluted with 0%-30% EtOAc in hexane) to give ethyl 2-(4-bromophenoxy)imidazo[1,2-a]pyridine-3-carboxylate (1.5 g) as a colorless solid and 2-(4-bromophenoxy)imidazo[1,2-a]pyridine (530 mg) as a colorless solid. The mixture of 2-(4-bromophenoxy)imidazo[1,2-a]pyridine (410 mg), 1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-one (164 mg), trans-N,N′-dimethylcyclohexane-1,2-diamine (174 mg), copper(I) iodide (116 mg), K2CO3 (338 mg) and THF(dry) (5 mL) was heated at 180° C. for 3 h under microwave irradiation. The solid was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexane) to give the title compound (72 mg) as an orange solid (mixture with 1,3-dihydro-2H-pyrrolo[2,3-b]pyridine-2-one, ca. 20% purity).

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography (silica gel, EtOAc/hexane)

Sources & evidence

ORD record
ord-a62327a1f735490d9b2d48c8d9efc182
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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