Sodium hydride → HCID 59593331, compound

HRID 2261555Notes

Reaction equation

HRID 2261555 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH:22]([Si:25](Cl)([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])([CH3:24])[CH3:23].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:22]([CH3:24])[CH3:23])[CH:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 516892Sodium BicarbonateHCID 59593338HCID 59593338, compound

Product 1

HCID 59593331HCID 59593331, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a clear solution of 3-(6-chloro-2-methoxypyridin-3-ylmethyl)-1H-pyrrolo[2,3-b]pyridine (28, 0.516 g, 1.88 mmol) in dimethylformamide (10 mL) was added sodium hydride (60% dispersion, 0.113 g, 2.82 mmol). After stirring at room temperature for 30 minutes, triisopropylsilyl chloride (600 μL, 2.83 mmol) was added. The reaction was stirred at room temperature for 2 hours, then poured into aqueous (1 M) sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried (magnesium sulfate), filtered and volatiles were removed by rotary evaporation to give a crude solid. The compound was purified by silica gel column chromatography eluting with 2% ethyl acetate in hexanes. This provided 732 mg of the desired compound as a white, crystalline solid (29, 1.70 mmol, 90%). MS (ESI) [M+H+]+=430.2.

Workup

  1. stirringThe reaction was stirred at room temperature for 2 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. customvolatiles were removed by rotary evaporation
  7. customto give a crude solid
  8. customThe compound was purified by silica gel column chromatography
  9. washeluting with 2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-55b2ddda009947fa8826ec2f2e0cfea3
Source dataset
uspto-grants-2010_12
Patent number
US07846941B2

Reaction notes

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