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Cesium carbonate → 4-Pyridinecarbonitrile, 2-methoxy-6-[4-(trifluoromethyl)phenyl]-

HRID 1479868
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HRID 1479868 반응식
Cl[C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([C:8]#[N:9])[CH:7]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=2)[N:3]=1
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 585038662-Chloro-6-methoxyisonicotinonitrile

생성물 1

HCID 903904274-Pyridinecarbonitrile, 2-methoxy-6-[4-(trifluoromethyl)phenyl]-수율 25%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매
HCID 312751,4-Dioxane용매

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온도
100 °C

실험 절차

The nitrile 25F (2.3 g, 13.8 mmol), 4-trifluoromethylphenylboronic acid (2.61 g, 1.1 mol eq), palladium acetate (62 mg, 0.02 mol eq), cesium carbonate (8.97 g, 2 mol eq), and XPhos (260 mg, 0.04 mol eq) were mixed, placed under a nitrogen atmosphere and dioxane (10 mL) was added. The mixture was heated at 100° C. for 4 h. After cooling, the mixture was filtered through a celite pad, washed with dioxane (2×30 mL) and concentrated under reduced pressure. The residue was purified by flash chromatography (9:1 petroleum ether:EtOAc) to afford 26I as a pale yellow solid (840 mg, 25% Yield). 1HNMR (DMSO, 200 MHz) δ 4.03 (s, 3H), 7.46 (s, 1H), 7.90 (d, 2H, J=7.8), 8.17 (s, 1H), 8.40 (d, 2H, J=8).

후처리

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered through a celite pad
  3. washwashed with dioxane (2×30 mL)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (9:1 petroleum ether:EtOAc)

출처 및 근거

ORD 기록
ord-b880c3d143954ca4a4cedc21f787d983
출처 데이터셋
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09409864B2

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