Water → 7-Chloro-1-isobutyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine

HRID 1932328Notes

Reaction equation

HRID 1932328 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[CH:6][CH:7]=[C:8]2[C:12]([CH3:13])=[C:11]([CH3:14])[NH:10][C:9]=12.I[CH2:16][CH:17]([CH3:19])[CH3:18].O>O1CCCC1>[Cl:3][C:4]1[N:5]=[CH:6][CH:7]=[C:8]2[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]([CH2:16][CH:17]([CH3:19])[CH3:18])[C:9]=12

Participants

6

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 116369277-Chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine

Product 1

HCID 117014497-Chloro-1-isobutyl-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridineYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60%, 33 mg, 0.83 mmol) was added to a solution of 7-chloro-2,3-dimethyl-1H-pyrrolo[2,3-c]pyridine (100 mg, 0.53 mmol) prepared in Step 1 in anhydrous tetrahydrofuran (2.8 ml). The reaction mixture was stirred for 30 minutes at room temperature. 1-Iodo-2-methylpropane (64 μl, 0.67 mmol) was added to the reaction mixture, which was then stirred overnight at room temperature. Water was added to the reaction mixture, which was then extracted with dichloromethane. The organic layer was dried on anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/9, v/v) to give 108 mg of the titled compound as a white solid. (Yield: 86%)

Workup

  1. stirringwas then stirred overnight at room temperature
  2. extractionwas then extracted with dichloromethane
  3. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/9, v/v)

Sources & evidence

ORD record
ord-f691ef001d2448a992ab4e261ebd37b1
Source dataset
uspto-grants-2012_05
Patent number
US08188114B2

Reaction notes

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