Nitrogen → HCID 86658649, compound

HRID 1875425Notes

Reaction equation

HRID 1875425 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][NH:8][C:7]=12.[H-].[Na+].N#N.I[CH2:16][CH3:17]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[CH:10]=[CH:9][N:8]([CH2:16][CH3:17])[C:7]=12

Participants

6

Reactant 4

HCID 947NitrogenHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 114350487-Chloro-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 86658649HCID 86658649, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-chloro-1H-pyrrolo[2,3-c]pyridine (11 mmol) in dry DMF (20 mL) was cooled on an ice bath, NaH (143 mmol) was added portion wise under N2. The mixture was allowed to stir at room temperature for 1 hr. Upon cooling to 0° C., iodoethane (26 mmol) was added and the mixture was reacted for further 3 his. After quenching with H2O (20 mL), the mixture was diluted with diethyl ether and extracted with ether (4×50 mL). The organic layers were combined, washed with brine, dried with MgSO4 and filtered. The solvent was evaporated to give 7-chloro-1-ethyl-1H-pyrrolo[2,3-c]pyridine as orange oil. MS (ESI+) m/z 181.0533 (M+H)+.

Workup

  1. temperaturewas cooled on an ice bath
  2. temperatureUpon cooling to 0° C.
  3. customthe mixture was reacted for further 3 his
  4. customAfter quenching with H2O (20 mL)
  5. additionthe mixture was diluted with diethyl ether
  6. extractionextracted with ether (4×50 mL)
  7. washwashed with brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-c0ff911bedd4470285230a0ec4dc014a
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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