Cesium carbonate → 5-[5-(2-Ethyl-3-formylphenyl)-1,3-thiazol-2-yl]-2-(2-methylpropyl)benzonitrile

HRID 1942663노트

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HRID 1942663 반응식
Br[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][CH:3]=1.[CH2:19]([C:21]1[C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][CH:26]=[CH:25][C:22]=1[CH:23]=[O:24])[CH3:20].C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH2:19]([C:21]1[C:22]([CH:23]=[O:24])=[CH:25][CH:26]=[CH:27][C:28]=1[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([CH2:15][CH:16]([CH3:18])[CH3:17])=[C:11]([CH:14]=2)[C:12]#[N:13])=[N:4][CH:3]=1)[CH3:20]

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 584940852-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehydeHCID 584940975-(5-Bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile

생성물 1

HCID 866590095-[5-(2-Ethyl-3-formylphenyl)-1,3-thiazol-2-yl]-2-(2-methylpropyl)benzonitrile수율 188.2%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
120 °C

실험 절차

To a solution of 5-(5-bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D91) (1.1 g), 2-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (D5) (443 mg) and Cs2CO3 (1.12 g) in 1,2-dimethoxyethane (DME) (15 mL) and water (3 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (2.80 g) in one charge. The reaction vessel was sealed and heated under microwave at 120° C. for 1.5 h. After cooling the reaction, the reaction mixture was filtered through silica gel and the filtrate was washed with aqueous saturated ammonium chloride and saturated brine. The organic phase was collected and dried over anhydrous sodium sulphate. After concentration, the crude product was purified by column chromatography to give 5-[5-(2-ethyl-3-formylphenyl)-1,3-thiazol-2-yl]-2-(2-methylpropyl)benzonitrile (D92) (1.2 g). MS (ES): C23H22N2OS requires 374. found 375.1 (M+H+).

후처리

  1. additioncharge
  2. customThe reaction vessel was sealed
  3. temperatureAfter cooling
  4. customthe reaction
  5. filtrationthe reaction mixture was filtered through silica gel
  6. washthe filtrate was washed with aqueous saturated ammonium chloride and saturated brine
  7. customThe organic phase was collected
  8. dry with materialdried over anhydrous sodium sulphate
  9. concentrationAfter concentration
  10. customthe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-5b82af0d0ee6449d83a82cd382026973
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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