Sodium Methoxide → 5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine

HRID 1515681Notes

Reaction equation

HRID 1515681 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([CH2:19]Cl)[CH:18]=[C:13]3[CH:12]=[CH:11]2)(=O)=O)C=CC=CC=1.[CH3:21][O-:22].[Na+]>CO.C(OCC)(=O)C>[CH3:21][O:22][CH2:19][C:17]1[CH:18]=[C:13]2[CH:12]=[CH:11][NH:10][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 672282211-benzenesulfonyl-5-chloromethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672290005-methoxymethyl-1H-pyrrolo[2,3-b]pyridineYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-benzenesulfonyl-5-chloromethyl-1H-pyrrolo[2,3-b]pyridine (3.3 g, 10.76 mmol) in methanol (15 mL) was added sodium methoxide (1.74 g, 32.3 mmol) at room temperature and the resulting mixture was stirred for 12 h. The mixture was diluted with ethyl acetate (250 mL), washed with brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 5-methoxymethyl-1H-pyrrolo[2,3-b]pyridine (1.74 g, quant.) as a light yellow solid which was used in the next step without further purification: LC/MS m/e calcd for C9H10N2O [M+H]+ 163.19, observed 162.9.

Workup

  1. washwashed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e9148bc404943b0868254ebc11e6e54
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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