Acetic Acid → 3-Methyl-1H-pyrrolo[2,3-b]pyridine-2-methanol

HRID 1756097Notes

Reaction equation

HRID 1756097 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.C(O)(=[O:16])C>>[OH:16][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

4

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 125323872,3-Dimethyl-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 193926133-Methyl-1H-pyrrolo[2,3-b]pyridine-2-methanol

Procedure

2,3-dimethylpyrrolo[2,3-b]pyridine(0,2 g 0.0014 mol) was treated in 3 ml acetic acid with an equimolecular amount of bromine and after 5 min yellow precipitate was formed. The solid was filtered off and treated with 3 ml water for 60 min. The mixture was made alkaline with bicarbonate and extracted with methylene chloride. When the organic layer had been dried and evaporated the product was isolated as a yellow oil. (0,12 g, 53%).

Workup

  1. customwas formed
  2. filtrationThe solid was filtered off
  3. additiontreated with 3 ml water for 60 min
  4. extractionextracted with methylene chloride
  5. customWhen the organic layer had been dried
  6. customevaporated the product
  7. customwas isolated as a yellow oil

Sources & evidence

ORD record
ord-894ed8647be240239f4f82179347125c
Source dataset
uspto-grants-1995_08
Patent number
US05439917

Reaction notes

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