2-Methyl-2-butene → 1H-Pyrrolo(2,3-b)pyridine-3-carboxylic acid

HRID 1766150Notes

Reaction equation

HRID 1766150 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.CC(=CC)C.Cl([O-])=[O:18].[Na+].P(O)(O)([O-])=O.[Na+]>O.O1CCOCC1>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:18])=[O:11])=[CH:2]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 101541911H-Pyrrolo(2,3-b)pyridine-3-carboxylic acidYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

2.3 g (15.7 mmol) of 1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde and 23 cm3 (217 mmol) of 2-methyl-2-butene were added to 120 cm3 of dioxane at a temperature of 20° C. and then a solution of 2.7 g (30 mmol) of sodium chlorite and 9.2 g (66.7 mmol) of monosodium phosphate in 100 cm3 of water was added. After stirring at a temperature in the region of 20° C. for 15 h, the reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa). The residue was taken up in 50 cm3 of water, filtered off, rinsed with 3 times 30 cm3 of water and then dried under a hood for 16 h. 2.2 g of 1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid were thus obtained in the form of a white powder. Mass spectrum: EI: m/z=162 M+ base peak.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure (2.7 kPa)
  2. filtrationfiltered off
  3. washrinsed with 3 times 30 cm3 of water
  4. customdried under a hood for 16 h

Sources & evidence

ORD record
ord-b87c55b3967e44ee9e5bd04a88427368
Source dataset
uspto-grants-2007_06
Patent number
US07230007B2

Reaction notes

Loading…