1,10-Phenanthroline → 2-(5-Bromo-2-pyridinyl)benzoxazole

HRID 521547

反応式

HRID 521547 の反応式
Br[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16](Cl)=[O:17])=[N:14][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.C(Cl)Cl.O1CCOCC1>[Br:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[O:17][C:2]3[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=3[N:4]=2)=[N:14][CH:15]=1

参加物

8

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 119922-BromoanilineHCID 190907715-Bromo-pyridine-2-carbonyl chloride

生成物 1

HCID 469416132-(5-Bromo-2-pyridinyl)benzoxazole収率 30%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-bromoaniline (3.90 g, 22.7 mmol), 5-bromopyridine-2-carbonyl chloride (5.00 g, 22.7 mmol), Cs2CO3 (14.78 g, 45.36 mmol), 1,10-phenanthroline (0.409 g, 2.27 mmol), CuI (0.216 g, 1.13 mmol) and anhydrous 1,4-dioxane (40 mL) was degassed with argon for about 40 min while stirring. The stirring reaction mixture was then maintained under argon at about 120° C. for about 40 h. Upon completion, the reaction was cooled to RT and poured over CH2Cl2 (300 mL). The organics were then washed with sat. NaHCO3, H2O and brine, dried over MgSO4, filter and concentrated in vacuo. Purification of the crude product via flash chromatography (SiO2, 4:1 dichloromethane-hexanes) and subsequent recrystallization from hexanes afforded compound 11 (1.86 g, 30% yield) as colorless fibers.

後処理

  1. customwas degassed with argon for about 40 min
  2. customThe stirring reaction mixture
  3. temperatureUpon completion, the reaction was cooled to RT
  4. washThe organics were then washed with sat. NaHCO3, H2O and brine
  5. dry with materialdried over MgSO4
  6. filtrationfilter
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude product

出典と根拠

ORDレコード
ord-3c0af32c96b544d6aa712ca19029fe13
出典データセット
uspto-grants-2016_05
特許番号
US09328086B2

関連ノート

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