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

HRID 452678노트

반응식

HRID 452678 반응식
[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

참가 물질

5

반응물 3

HCID 66221Triethyl orthoacetateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 686635833-Bromofuro[3,2-b]pyridine-5-carbohydrazide

생성물 1

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

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ca2d4045b6a14c58b26a8cd6a24f503f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492378B2

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