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

HRID 452678ノート

反応式

HRID 452678 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ca2d4045b6a14c58b26a8cd6a24f503f
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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