Triethyl orthoacetate → 3-Bromo-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridine

HRID 452678Notes

Reaction equation

HRID 452678 reaction equation
[Br:1][C:2]1[C:6]2=[N:7][C:8]([C:11]([NH:13][NH2:14])=[O:12])=[CH:9][CH:10]=[C:5]2[O:4][CH:3]=1.[C:15](OCC)(OCC)(OCC)[CH3:16].N12CCCN=C1CCCCC2>C(O)CCC>[Br:1][C:2]1[C:6]2=[N:7][C:8]([C:11]3[O:12][C:15]([CH3:16])=[N:14][N:13]=3)=[CH:9][CH:10]=[C:5]2[O:4][CH:3]=1

Participants

5

Reactant 3

HCID 66221Triethyl orthoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 68663583HCID 68663583, compound

Product 1

HCID 686630993-Bromo-5-(5-methyl-1,3,4-oxadiazol-2-yl)furo[3,2-b]pyridineYield 23%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 3-bromofuro[3,2-b]pyridine-5-carbohydrazide (0.16 g, 0.64 mmol) and triethyl orthoacetate (0.26 mL, 1.40 mmol) in n-butanol (3 mL) was heated under reflux for 1 hr. 1,8-Diazabicyclo[5.4.0]undec-7-ene (0.096 mL, 0.64 mmol) was added to the reaction mixture, and the resulting mixture was heated under reflux overnight. After cooling, the precipitate was collected by filtration, purified by silica gel column chromatography (hexane/ethyl acetate=3/1), and recrystallized from hexane/ethyl acetate to give the title compound (41 mg, yield 23%) as colorless crystals.

Workup

  1. temperatureunder reflux for 1 hr
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux overnight
  4. temperatureAfter cooling
  5. filtrationthe precipitate was collected by filtration
  6. custompurified by silica gel column chromatography (hexane/ethyl acetate=3/1)
  7. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-ca2d4045b6a14c58b26a8cd6a24f503f
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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