Cesium carbonate → HCID 58446983、化合物

HRID 1045729ノート

反応式

HRID 1045729 の反応式
Br[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)[C:5]2[N:6]([CH:8]=[N:9][N:10]=2)[CH:7]=1.[S:24]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25]1.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>[S:24]1[CH:28]=[CH:27][C:26]([C:2]2[N:3]=[C:4]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:5]3[N:6]([CH:8]=[N:9][N:10]=3)[CH:7]=2)=[CH:25]1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 581760Thiophene-3-boronic acidHCID 58447041HCID 58447041、化合物

生成物 1

HCID 58446983HCID 58446983、化合物収率 99.5%

試薬・触媒・溶媒 2

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

実験手順

A 100 mL round bottom flask was charged with tert-butyl 4-(6-bromo-[1,2,4]triazolo[4,3-a]pyrazin-8-yl)piperazine-1-carboxylate (1.0 g, 2.6 mmol), thiophen-3-ylboronic acid (0.50 g, 3.9 mmol), Pd(PPh3)4 (0.30 g, 0.26 mmol), Cs2CO3 (1.27 g, 3.9 mmol), 1,4-dioxane (25 mL) and water (25 mL). The resulting mixture was refluxed under N2 overnight. Reaction progress was monitored by TLC (EtOAc/petroleum ether=1:2). Work-up: the reaction mixture was extracted with EtOAc (50 mL). The organic solution was washed with brine (40 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether, to afford 1.0 g (99%) of the product as a yellow solid.

後処理

  1. temperatureThe resulting mixture was refluxed under N2 overnight
  2. customReaction progress
  3. extractionthe reaction mixture was extracted with EtOAc (50 mL)
  4. washThe organic solution was washed with brine (40 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was further purified by flash column chromatography on silica gel with 10% EtOAc in petroleum ether

出典と根拠

ORDレコード
ord-a29df5a0eb884f37a31cb889c6d84382
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…