Water → HCID 86658646, compound

HRID 1875422Notes

Reaction equation

HRID 1875422 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][NH:10][C:5]2=[C:4]([CH3:11])[CH:3]=1.[H-].[Na+].I[CH2:15][CH2:16][CH3:17].O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]2[CH:8]=[CH:9][N:10]([CH2:15][CH2:16][CH3:17])[C:5]2=[C:4]([CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 110302085-Chloro-7-methyl-1H-pyrrolo[3,2-B]pyridine

Product 1

HCID 86658646HCID 86658646, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-chloro-7-methyl-1H-pyrrolo[3,2-b]pyridine (5 mmol) in dry DMF (10 mL) cooling on an ice bath was treated with NaH (60 mmol) under N2. After stirring at room temperature for 45 minutes iodopropane (10 mmol) was added. The mixture was allowed to react for further 3 hrs. Upon cooling on an ice bath it was treated with H2O (3 mL). The mixture was then extracted with diethyl ether (4×50 mL). The ether layers were combined, washed with brine, dried on MgSO4 and filtered. The solvent was evaporated to give 5-chloro-7-methyl-1-propyl-1H-pyrrolo[3,2-b]pyridine as orange oil. 1H-NMR (DMSO-d6) δ: 0.85 (t, 3H, J=7.6 Hz, CH3), 1.75 (m, 2H, CH2), 4.28 (t, 2H, J=7.6 Hz, CH2), 6.48 (d, 1H, J=3.2 Hz, Ar—H), 6.97 (s, 1H, Ar—H), 7.66 (d, 1H, J=3.6 Hz, Ar—H). MS (ESI+) m/z 209.0648 (M+H)+.

Workup

  1. additionwas added
  2. customto react for further 3 hrs
  3. temperatureUpon cooling on an ice bath it
  4. extractionThe mixture was then extracted with diethyl ether (4×50 mL)
  5. washwashed with brine
  6. customdried on MgSO4
  7. filtrationfiltered
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a87a4af230214d57a629bf137fb07af7
Source dataset
uspto-grants-2012_11
Patent number
US08309550B2

Reaction notes

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