6-Azaindole → HCID 67447567, compound

HRID 1875430Notes

Reaction equation

HRID 1875430 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[H-].[Na+].I[CH2:13][CH2:14][CH3:15]>CN(C=O)C>[CH2:13]([N:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1)[CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 92196-AzaindoleHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 67447567HCID 67447567, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1H-pyrrolo[2,3-c]pyridine (10 mmol) in DMF cooling on an ice bath was treated with NaH (143 mmol). After stirred at room temperature for thr iodopropane (26 mmol) was added dropwise. The mixture was allowed to react at room temperature for further 3 hrs. Upon cooling on an ice bath the mixture was quenched with 20 mL H2O, followed by extraction with diethyl ether (5×50 mL). The organic layers were combined, washed with brine, dried on MgSO4 and filtered. The solvent was evaporated and dried on a high vacuum to give 1-propyl-1H-pyrrolo[2,3-c]pyridine as orange oil. MS (ESI+) m/z 161.1063 (M+H)+.

Workup

  1. additionwas added dropwise
  2. customto react at room temperature for further 3 hrs
  3. temperatureUpon cooling on an ice bath the mixture
  4. customwas quenched with 20 mL H2O
  5. extractionfollowed by extraction with diethyl ether (5×50 mL)
  6. washwashed with brine
  7. customdried on MgSO4
  8. filtrationfiltered
  9. customThe solvent was evaporated
  10. customdried on a high vacuum

Sources & evidence

ORD record
ord-3d08893f29544649810cc6b74c8c2f00
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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