Methanol → 2-Methoxymethyl-3-methylpyrrolo[2,3-b]pyridine

HRID 1756102Notes

Reaction equation

HRID 1756102 reaction equation
[CH3:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11].BrBr.[CH3:14][OH:15]>C(O)(=O)C>[CH3:14][O:15][CH2:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH3:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 24408BromineHCID 125323872,3-Dimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 199168132-Methoxymethyl-3-methylpyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2,3-dimethylpyrrolo[2,3-b]pyridine 0,5 g (0.0034 mol) was treated in 7 ml acetic acid with an equimolecular amount of bromine and after 5 min a yellow precipitate was formed. The solid was filtred off and treated with 20 ml methanol. The mixture was refluxed for 30 min. and was then evaporated. The residue was partitioned between methylene chloride and bicarbonate solution. The organic layer was separated dried over Na2SO4 and evaporated. The residue was treated with boiling petroleumether (60-80) which was decantated and allowed to cool. The precipitated product was filtred off affording 0,13 g (22%) as white solid.

Workup

  1. customwas formed
  2. temperatureThe mixture was refluxed for 30 min.
  3. customwas then evaporated
  4. customThe residue was partitioned between methylene chloride and bicarbonate solution
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. additionThe residue was treated
  9. temperatureto cool
  10. customaffording 0,13 g (22%) as white solid

Sources & evidence

ORD record
ord-ae977cdfeef04f3f985222e37e3709fc
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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