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

HRID 1045721노트

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HRID 1045721 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매

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온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-253db3cef78643d1bb071e927acd7f4c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569300B2

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