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

HRID 876782Notes

Reaction equation

HRID 876782 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[H-].[Na+].[CH3:16][Si:17]([CH2:20][CH2:21][O:22][CH2:23]Cl)([CH3:19])[CH3:18].O>C1COCC1>[CH3:16][Si:17]([CH3:19])([CH3:18])[CH2:20][CH2:21][O:22][CH2:23][N:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 17390026methyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Product 1

HCID 67306524Methyl 1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylateYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1H-pyrrolo[2,3-b]pyridine-2-carboxylate (H-1) (528 mg, 3 mmol) in dried THF (5 mL) at 0° C. was added NaH (240 mg, 6 mmol). The reaction was stirred for 0.5 h under N2, and then SEMCl (526 mg, 3 mmol) was added dropwise. The mixture was stirred at room temperature for 2 h. H2O was added to quench the reaction. The resulting mixture was extracted with EtOAc. The oragnic layer was dried over Na2SO4, and concentrated to afford the title compound (750 mg), which was used for the next step without purification. MS (m/z): 307 (M+1)+.

Workup

  1. stirringThe mixture was stirred at room temperature for 2 h
  2. customto quench
  3. customthe reaction
  4. extractionThe resulting mixture was extracted with EtOAc
  5. dry with materialThe oragnic layer was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d7a0a90f334b4fa99ba4a7b25beff750
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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