1H-Pyrrolo(2,3-b)pyridine → HCID 58217085, compound

HRID 1035474Notes

Reaction equation

HRID 1035474 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[NH:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1.[C:14](Cl)(=[O:19])[C:15]#[C:16][CH2:17][CH3:18].C(=O)([O-])O.[Na+]>ClCCl>[NH:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14](=[O:19])[C:15]#[C:16][CH2:17][CH3:18])=[CH:6]1

Participants

6

Reactant 4

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 13951202Pent-2-ynoyl chloride

Product 1

HCID 58217085HCID 58217085, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.1 5.6 g (42.0 mmol) of aluminium trichloride are added to a solution of 1.0 g (8.47 mmol) of pyrrolo[2,3-b]pyridine in 100 ml of dichloromethane, and the mixture is stirred at room temperature for 2 h. 52 ml (0.2 M, 10.09 mmol) of pent-2-ynoyl chloride dissolved in dichloromethane are then slowly added dropwise to the reaction solution. The mixture is left to stir at room temperature for a further 16 h. Saturated sodium hydrogencarbonate solution is added to the reaction mixture until neutral, and the aluminium salt precipitate is filtered off with suction. The aqueous phase is separated off and extracted twice with dichloromethane. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The residue is employed in the next reaction without further purification. 1-(1H-Pyrrolo[2,3-b]pyridin-3-yl)pent-2-yn-1-one (74% purity) is obtained as colourless oil; ESI 199.

Workup

  1. additionare then slowly added dropwise to the reaction solution
  2. waitThe mixture is left
  3. stirringto stir at room temperature for a further 16 h
  4. filtrationis filtered off with suction
  5. customThe aqueous phase is separated off
  6. extractionextracted twice with dichloromethane
  7. washThe combined organic phases are washed with saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. customevaporated
  10. customThe residue is employed in the next reaction without further purification

Sources & evidence

ORD record
ord-7bde2ac6112c4184b4df361276e2f416
Source dataset
uspto-grants-2013_10
Patent number
US08546390B2

Reaction notes

Loading…