Cesium carbonate → 8-Methoxy-5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine

HRID 1045721ノート

反応式

HRID 1045721 の反応式
Br[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([O:11][CH3:12])=[N:4][CH:3]=1.[S:13]1[CH:17]=[CH:16][CH:15]=[C:14]1B(O)O.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH3:12][O:11][C:5]1[C:6]2[N:7]([CH:8]=[N:9][N:10]=2)[C:2]([C:14]2[S:13][CH:17]=[CH:16][CH:15]=2)=[CH:3][N:4]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27339602-Thiopheneboronic acidHCID 584469805-Bromo-8-methoxy-[1,2,4]triazolo[4,3-A]pyrazine

生成物 1

HCID 584470378-Methoxy-5-(thiophen-2-yl)-[1,2,4]triazolo[4,3-a]pyrazine収率 99%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A 50 mL round bottom flask was charged with 5-bromo-8-methoxy-[1,2,4]triazolo[4,3-a]pyrazine (0.25 g, 1.1 mmol), thiophen-2-ylboronic acid (280 mg, 2.2 mmol), Pd(PPh3)4 (190 mg, 0.16 mmol), Cs2CO3 (530 mg, 1.6 mmol), 1,4-dioxane (11 mL) and water (4 mL). The resulting mixture was heated under N2 at 100° C. overnight. Work-up: the reaction mixture was filtered. The filter cake was washed with EtOAc (10 mL) and the filtrate was extracted with more EtOAc (10 mL×3). The combined organic solutions were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a 1:50 methanol/dichloromethane, to afford 0.25 g (99%) of the product as a yellow solid. MS m/z: 233 (M+H+).

後処理

  1. filtrationthe reaction mixture was filtered
  2. washThe filter cake was washed with EtOAc (10 mL)
  3. extractionthe filtrate was extracted with more EtOAc (10 mL×3)
  4. washThe combined organic solutions were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography on silica gel with a 1:50 methanol/dichloromethane

出典と根拠

ORDレコード
ord-253db3cef78643d1bb071e927acd7f4c
出典データセット
uspto-grants-2013_10
特許番号
US08569300B2

反応ノート

読み込み中…