Methyl iodide → 6-Methoxy-1H-pyrrolo[2,3-b]pyridine

HRID 273331Notes

Reaction equation

HRID 273331 reaction equation
[NH:1]1[C:5]2=[N:6][C:7]([OH:10])=[CH:8][CH:9]=[C:4]2[CH:3]=[CH:2]1.[C:11]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:11][O:10][C:7]1[N:6]=[C:5]2[NH:1][CH:2]=[CH:3][C:4]2=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178515692HCID 178515692, compound

Product 1

HCID 116151916-Methoxy-1H-pyrrolo[2,3-b]pyridineYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1H-pyrrolo[2,3-b]pyridin-6-ol (0.200 g, 1.49 mmol) and K2CO3 (1 g, 7.45 mmol) in acetone (30 mL) was stirred under N2 at room temperature for 1 h. MeI (0.166 g, 1.192 mmol) was added. The reaction mixture was stirred under N2 at 50° C. for 12 h and then filtered. The filtrate was concentrated to half its volume, diluted with water, and extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, and evaporated to give a residue, which was purified on a column of silica gel eluting with EtOAc/hexane (1:4) to give 6-methoxy-1H-pyrrolo[2,3-b]pyridine (159 mg, 89%).

Workup

  1. stirringThe reaction mixture was stirred under N2 at 50° C. for 12 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to half its volume
  4. additiondiluted with water
  5. extractionextracted with CH2Cl2
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. customevaporated
  8. customto give a residue, which
  9. customwas purified on a column of silica gel eluting with EtOAc/hexane (1:4)

Sources & evidence

ORD record
ord-6491a58bc9574c9da7db5d60ee9f6eb1
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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