Pyridine → HCID 14447204, compound

HRID 1854670Notes

Reaction equation

HRID 1854670 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1.N1C=CC=CC=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>ClCCl.C(OCC)(=O)C>[C:18]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH:10]=[O:11])[CH:8]=2)[CH:3]=[CH:2]1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 27734351H-Indole-6-carboxaldehyde

Product 1

HCID 14447204HCID 14447204, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1H-indole-6-carboxaldehyde (300 mg, 2.07 mmol) in 6.2 mL of dry dichloromethane were added pyridine (0.34 mL, 4.2 mmol), acetic anhydride (1.77 mL, 18.7 mmol), and N,N-dimethylaminopyridine (60 mg, 0.49 mmol) at room temperature, successively. After being stirred at room temperature overnight, the reaction mixture was diluted with ethyl acetate. The solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid was rinsed with diethyl ether/hexane to obtain the title compound as a pale orange powder (267 mg, 69%).

Workup

  1. washThe solution was washed with 1N HCl, saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe resulting solid was rinsed with diethyl ether/hexane

Sources & evidence

ORD record
ord-c6f0a1862ac04410b7f265e02aab3f74
Source dataset
uspto-grants-2015_02
Patent number
US08962674B2

Reaction notes

Loading…