Formaldehyde → N,N-Dimethyl-1H-pyrrolo[3,2-b]pyridine-3-methanamine

HRID 731586Notes

Reaction equation

HRID 731586 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.[CH3:11][NH:12][CH3:13].[CH2:14]=O>C(O)CCC>[CH3:11][N:12]([CH2:14][C:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[NH:1][CH:2]=1)[CH3:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 92264-AzaindoleHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 12146847N,N-Dimethyl-1H-pyrrolo[3,2-b]pyridine-3-methanamineYield 64%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-azaindole (0.880 g, 7.45 mmol), dimethylamine hydrochloride (0.67 g, 8.19 mmol) and paraformaldehyde (0.25 g, 8.19 mmol eq.) in 1-butanol is heated at reflux temperature for 3 h, cooled, concentrated in vacuo, treated with water and saturated aqueous NaHCO3 and extracted with 4:1 CH2Cl2:ethanol. The combined extracts are dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed (silica gel, ethyl acetate, followed by 5:95 triethylamine:ethanol as eluent) to afford the title compound as a tan solid, 0.838 g (64% yield), identified by NMR analysis.

Workup

  1. temperatureat reflux temperature for 3 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. additiontreated with water and saturated aqueous NaHCO3
  5. extractionextracted with 4:1 CH2Cl2
  6. dry with materialThe combined extracts are dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is chromatographed (silica gel, ethyl acetate, followed by 5:95 triethylamine:ethanol as eluent)

Sources & evidence

ORD record
ord-6a8ec4ee7eaa46f2be26a0ffd44c59d1
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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