Formaldehyde → 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 3-[(dimethylamino)methyl]-

HRID 1952170Notes

Reaction equation

HRID 1952170 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=[C:4]2[CH:3]=[CH:2]1.Cl.[CH3:13][NH:14][CH3:15].[CH2:16]=O>C(O)(C)C>[CH3:13][N:14]([CH2:16][C:3]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]([C:10]#[N:11])[CH:9]=2)[NH:1][CH:2]=1)[CH3:15]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 117883551H-Pyrrolo[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 576193521H-Pyrrolo[2,3-b]pyridine-5-carbonitrile, 3-[(dimethylamino)methyl]-Yield 48%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To 1H-Pyrrolo[2,3-b]pyridine-5-carbonitrile (632, 3.00 g, 0.0210 mol) in isopropyl alcohol (120 mL) were added dimethylamine hydrochloride (1.91 g, 0.0235 mol) and formaldehyde (0.708 g, 0.0236 mol). The reaction was heated to reflux overnight, then concentrated, poured into water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% to 30% methanol in dichloromethane containing 0.3% triethyl amine to give the desired compound (633, 2.0 g, 48%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. additionpoured into water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. custompurified by silica gel column chromatography
  10. washeluting with 5% to 30% methanol in dichloromethane containing 0.3% triethyl amine

Sources & evidence

ORD record
ord-4a42006d7b3141658f04504fd29f026c
Source dataset
uspto-grants-2013_03
Patent number
US08404700B2

Reaction notes

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