Formaldehyde → Dimethyl-(1H-pyrrolo[3,2-c]pyridin-3-ylmethyl)-amine

HRID 731593Notes

Reaction equation

HRID 731593 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][N: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[CH:5]=[N:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1)[CH3:13]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 92205-AzaindoleHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 19013583Dimethyl-(1H-pyrrolo[3,2-c]pyridin-3-ylmethyl)-amineYield 39%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-azaindole (1.19 g, 10.0 mmol), dimethylamine hydrochloride (0.98 g, 12.0 mmol) and paraformaldehyde (0.36 g, 12.0 mmol-equivalents) in 1-butanol is heated at reflux temperature for 5 h and concentrated in vacuo. The concentrate is diluted with saturated aqueous NaHCO3 and extracted with 4:1 CH2Cl2:ethanol. The combined extracts are dried over MgSO4, concentrated in vacuo and filtered. The filtercake is air-dried to afford the title compound as a yellow solid, 0.680 g (39% yield), identified by NMR analysis.

Workup

  1. temperatureat reflux temperature for 5 h
  2. concentrationconcentrated in vacuo
  3. additionThe concentrate is diluted with saturated aqueous NaHCO3
  4. extractionextracted with 4:1 CH2Cl2
  5. dry with materialThe combined extracts are dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. filtrationfiltered
  8. customThe filtercake is air-dried

Sources & evidence

ORD record
ord-93ff17d6132f4ee4b2fc275086f372cc
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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