Water → 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

HRID 2042294Notes

Reaction equation

HRID 2042294 reaction equation
[H-].[Na+].[NH:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1.[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl.O>CN(C=O)C>[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][N:3]1[C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[CH:5]=[CH:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 584313511-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (934 mg, 0.0358 mol) in DMF (57 mL) was added dropwise under N2, a solution of 1H-pyrrolo[2,3-b]pyridine (3.00 g, 0.0254 mol) in DMF (20 mL). The mixture was stirred at r.t. for 45 min. then cooled to 0° C. and treated dropwise with [2-(trimethylsilyl)ethoxy]methyl chloride (6.32 mL, 0.0357 mol). The mixture was stirred at rt for 12 h. then poured into water (10 mL), stirred for 30 min. and extracted with Et2O (4×10 mL). The combined extracts were washed with brine (20 mL), dried over sodium sulfate, and concentrated in vacuo to give the crude product which was chromatographed over silica gel eluting with hexane→1:9 Et2O: hexane to afford 6 g desired product.

Workup

  1. additionwas added dropwise under N2
  2. temperaturethen cooled to 0° C.
  3. stirringThe mixture was stirred at rt for 12 h.
  4. stirringstirred for 30 min.
  5. extractionextracted with Et2O (4×10 mL)
  6. washThe combined extracts were washed with brine (20 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto give the crude product which
  10. customwas chromatographed over silica gel eluting with hexane→1:9 Et2O

Sources & evidence

ORD record
ord-aa8a627d44a146469546471880b971ee
Source dataset
uspto-grants-2013_11
Patent number
US08586546B2

Reaction notes

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