Sodium hydride → 4-chloro-2-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1360185Notes

Reaction equation

HRID 1360185 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9]([CH3:11])=[CH:10][C:3]=12.[H-].[Na+].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])[C:9]([CH3:11])=[CH:10][C:3]=12

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 210816754-Chloro-2-methyl-7-azaindole

Product 1

HCID 579286414-chloro-2-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridine (0.85 g) in N,N-dimethylformamide (8.5 ml) was added 60% oil-suspended NaH (245 mg) under nitrogen atmosphere while being cooled in an ice water bath. The reaction solution was stirred at ambient temperature for 1 hour and cooled again in the ice water bath. To the reaction solution was added triisopropylsilyl chloride (1.3 ml) slowly dropwise for 10 or more minutes. The reaction solution was stirred for 3 hours at ambient temperature and diluted with ethyl acetate (30 ml). The solution was washed with saturated aqueous sodium hydrogencarbonate (30 ml) and brine (20 ml). The solution was dehydrated with anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane) to obtain 4-chloro-2-methyl-1-(triisopropylsilyl)-pyrrolo[2,3-b]pyridine (1.45 g) as a colorless transparent liquid.

Workup

  1. temperaturewhile being cooled in an ice water bath
  2. stirringThe reaction solution was stirred for 3 hours at ambient temperature
  3. washThe solution was washed with saturated aqueous sodium hydrogencarbonate (30 ml) and brine (20 ml)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (n-hexane)

Sources & evidence

ORD record
ord-b23d7b94cd6842c7a2f056ac1889d1f2
Source dataset
uspto-grants-2011_02
Patent number
US07879844B2

Reaction notes

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