1H-Pyrrolo(2,3-b)pyridine → HCID 22028178, compound

HRID 731566Notes

Reaction equation

HRID 731566 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].Cl.[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16]Cl>CN(C=O)C>[CH3:13][N:14]([CH3:18])[CH2:15][CH2:16][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydrideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochloride

Product 1

HCID 22028178HCID 22028178, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 1H-pyrrolo[2,3-b]pyridine (5.00 g, 42.3 mmol) in DMF at ambient temperature is treated with 95% sodium hydride in oil (3.78 g, 150 mmol). After gas evolution subsides, the reaction mixture is treated with 2-(dimethylamino)-ethyl chloride hydrochloride (6.40 g, 44.4 mmol), stirred for 16 h and concentrated in vacuo. The resultant residue is partitioned between EtOAc and water. The organic phase is separated, dried over MgSO4 and concentrated in vacuo to afford the title compound as an oil, 6.50 g (81% yield), identified by HNMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is partitioned between EtOAc and water
  3. customThe organic phase is separated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3756e269d0fb487e9006ff2403cf2ada
Source dataset
uspto-grants-2009_09
Patent number
US07585873B2

Reaction notes

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