Potassium Carbonate → HCID 68184279, compound

HRID 2199971Notes

Reaction equation

HRID 2199971 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23]Cl>CN1CCCC1=O>[CH3:20][C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[C:22]=1[CH2:23][N:1]1[C:9]2[C:4](=[N:5][CH:6]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2211542,6-Dimethylbenzyl ChlorideHCID 11672756Methyl 1H-pyrrolo[3,2-b]pyridine-6-carboxylate

Product 1

HCID 68184279HCID 68184279, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of methyl 1H-pyrrolo[3,2-b]pyridin-6-carboxylate (50 mg) in N-methyl-2-pyrrolidone (1 mL) were added potassium carbonate (158 mg) and 2,6-dimethylbenzyl chloride (91 mg), and then the reaction mixture was subjected to microwave irradiation at 160° C. for 30 minutes. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (21 mg) as a white solid.

Workup

  1. customirradiation at 160° C. for 30 minutes
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5f57eea081f441d18e39f8ee159337d5
Source dataset
uspto-grants-2016_06
Patent number
US09359350B2

Reaction notes

Loading…