Potassium Carbonate → Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate

HRID 1521718Notes

Reaction equation

HRID 1521718 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+].Br[CH:27]([CH3:30])[C:28]#[N:29]>CN(C=O)C>[C:28]([CH:27]([N:1]1[C:5]2=[N:6][C:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:30])#[N:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1405382-BromopropionitrileHCID 67236396Diethyl 1H-pyrrolo[2,3-B]pyridine-2,6-dicarboxylate2×

Product 1

HCID 67236322Diethyl 1-(1-cyanoethyl)-1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylateYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl 1H-pyrrolo[2,3-b]pyridine-2,6-dicarboxylate (Intermediate D, 1.55 g, 5.91 mmol) in DMF (15 mL) is added potassium carbonate (2.45 g, 17.7 mmol), and the mixture is stirred at room temperature for 20 min. 2-bromopropionitrile (1.05 mL, 11.8 mmol) is added, the mixture is warmed to 80° C., and is stirred overnight. After being cooled to room temperature, the mixture is poured onto H2O, and the aqueous layer is extracted with EtOAc (3×100 mL). The combined organic extracts are dried (MgSO4), filtered, and concentrated. The crude material is purified via flash column chromatography using a gradient elution of 10-50% ethyl acetate/hexanes to afford the title compound as a bright yellow solid (809 mg, 43%).

Workup

  1. temperaturethe mixture is warmed to 80° C.
  2. stirringis stirred overnight
  3. temperatureAfter being cooled to room temperature
  4. additionthe mixture is poured onto H2O
  5. extractionthe aqueous layer is extracted with EtOAc (3×100 mL)
  6. dry with materialThe combined organic extracts are dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material is purified via flash column chromatography
  10. washa gradient elution of 10-50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3cf1058b80164a44a93a0dcc074f5606
Source dataset
uspto-grants-2015_07
Patent number
US09073926B2

Reaction notes

Loading…