Cesium carbonate → HCID 58446983, 화합물

HRID 1045729노트

반응식

HRID 1045729 반응식
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

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 581760Thiophene-3-boronic acidHCID 58447041HCID 58447041, 화합물

생성물 1

HCID 58446983HCID 58446983, 화합물수율 99.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a29df5a0eb884f37a31cb889c6d84382
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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