Sodium hydride → HCID 59593331, compound

HRID 1367282Notes

Reaction equation

HRID 1367282 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 (1M) sodium bicarbonate and extracted with ethyl acetate. The organic layer was separarted, 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. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. customvolatiles were removed by rotary evaporation
  6. customto give a crude solid
  7. customThe compound was purified by silica gel column chromatography
  8. washeluting with 2% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-84847808966845c7aad267ae2d472b11
Source dataset
uspto-grants-2011_02
Patent number
US07893075B2

Reaction notes

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