Cesium carbonate → N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amine

HRID 77476노트

반응식

HRID 77476 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[N:3]=1.[CH:19](B1OB(C=C)OB(C=C)O1)=[CH2:20].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.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>[F:16][C:15]([F:18])([F:17])[C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:4]2[N:3]=[C:2]([CH:19]=[CH2:20])[N:7]=[CH:6][N:5]=2)=[CH:10][CH:11]=1

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 2734807TrivinylboroxinHCID 860496674-chloro-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine

생성물 1

HCID 86679766N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amine수율 16.5%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 312751,4-Dioxane용매

반응 조건

온도
90 °C

실험 절차

To a solution of 4-chloro-N-(4-(trifluoromethyl)phenyl)-1,3,5-triazin-2-amine (0.5 g, 1.821 mmol) in dioxane (8 mL) and water (2 mL) were added trivinylboroxin (0.588 g, 3.64 mmol), cesium carbonate (1.780 g, 5.46 mmol). The reaction mixture was flushed with nitrogen for 10 min and Tetrakis (0.210 g, 0.182 mmol) was added. The reaction mixture was heated at 90° C. for 2 h then filtered through a pad of celite and washed with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel using 15% ethyl acetate in hexane to give N-(4-(trifluoromethyl)phenyl)-4-vinyl-1,3,5-triazin-2-amine as a white solid (0.08 g, 12.21% yield). LCMS: R.T.=1.14 min; [M+H]+=267.1.

후처리

  1. customThe reaction mixture was flushed with nitrogen for 10 min
  2. filtrationthen filtered through a pad of celite
  3. washwashed with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel using 15% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-96ca640b9c8c4eecbd011e645062e390
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841301B2

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