N-(6-Bromo-quinolin-2-ylmethyl)-acetamide → 7-Bromo-1-methyl-imidazo[1,5-a]quinoline

HRID 2075681Notes

Reaction equation

HRID 2075681 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][NH:13][C:14](=O)[CH3:15])[CH:6]=[CH:5]2>P(Cl)(Cl)(Cl)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:14]([CH3:15])=[N:13][CH:12]=[C:7]1[CH:6]=[CH:5]2

Participants

3

Reactant 1

HCID 67091079N-(6-Bromo-quinolin-2-ylmethyl)-acetamide

Product 1

HCID 670913757-Bromo-1-methyl-imidazo[1,5-a]quinoline

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

4c (213 mg, 0.82 mmol) was refluxed in phosphorus oxychloride (5 mL) for 1 hour. The mixture was cooled to room temperature, concentrated, and diluted with saturated aqueous NaHCO3 and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (50-100% EtOAc in hexanes) to give the desired product, 4d.

Workup

  1. concentrationconcentrated
  2. additiondiluted with saturated aqueous NaHCO3 and EtOAc
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (50-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-74f56c4a4bd749c6b6706af297154852
Source dataset
uspto-grants-2011_04
Patent number
US07919621B2

Reaction notes

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