Water → 1H-Pyrrolo[2,3-B]pyridine-3-methanamine, N,N-dimethyl-1-[tris(1-methylethyl)silyl]-

HRID 1261133Notes

Reaction equation

HRID 1261133 reaction equation
[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[H-].[Na+].[CH:16]([Si:19](Cl)([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([CH3:18])[CH3:17].O>CN(C)C=O>[CH3:1][N:2]([CH3:13])[CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:16]([CH3:18])[CH3:17])[CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Product 1

HCID 497589771H-Pyrrolo[2,3-B]pyridine-3-methanamine, N,N-dimethyl-1-[tris(1-methylethyl)silyl]-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dimethyl-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)-amine 109 (5.0 g, 28 mmol), was dissolved in N,N-dimethylformamide (80.0 mL) and sodium hydride (60% dispersion in mineral oil, 1.25 g, 31.4 mmol) was added, followed by triisopropylsilyl chloride (6.3 mL, 30.0 mmol). The reaction was stirred at room temperature for 12 hours, then poured into water and extracted with ethyl acetate. The organic portion was washed with brine, dried over sodium sulfate, concentrated and purified with silica gel chromatography to give the compound (110, 6.5 g, 70%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic portion was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified with silica gel chromatography
  6. customto give the compound (110, 6.5 g, 70%)

Sources & evidence

ORD record
ord-ed5943cb4434445d80f251aa6a7a8fcf
Source dataset
uspto-grants-2013_06
Patent number
US08470818B2

Reaction notes

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