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

HRID 1256847Notes

Reaction equation

HRID 1256847 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-fe585eb1ee6442aca2656d0d5299b694
Source dataset
uspto-grants-2013_06
Patent number
US08461169B2

Reaction notes

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