Water → 5-(5-Bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile

HRID 1942662노트

반응식

HRID 1942662 반응식
[CH3:1][CH:2]([CH3:21])[CH2:3][C:4]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][C:5]=1[C:6]#[N:7].Br[C:23]1[S:24][C:25]([Br:28])=[CH:26][N:27]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>COCCOC.C(OCC)(=O)C.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>[Br:28][C:25]1[S:24][C:23]([C:9]2[CH:10]=[CH:11][C:4]([CH2:3][CH:2]([CH3:1])[CH3:21])=[C:5]([CH:8]=2)[C:6]#[N:7])=[N:27][CH:26]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 3123942,5-DibromothiazoleHCID 51358167Benzonitrile, 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

생성물 1

HCID 584940975-(5-Bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile수율 59.2%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of 2-(2-methylpropyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D59) (600 mg), 2,5-dibromo-1,3-thiazole (767 mg), and Cs2CO3 (1028 mg) in 1,2-dimethoxyethane (DME) (10 mL)/water (2 mL) stirred under nitrogen at room temperature was added PdCl2(dppf)-CH2Cl2 adduct (344 mg). The reaction mixture was sealed and heated under microwave at 120° C. for 4 h. After cooling the reaction, the mixture was diluted with ethyl acetate and filtered through silical gel. The filtrate was washed with aqueous saturated ammonium chloride and saturated brine. The organic phase was collected and dried over anhydrous sodium sulphate. The solvent was removed in vacuo to give the crude product, which was purified by column chromatography to afford 5-(5-bromo-1,3-thiazol-2-yl)-2-(2-methylpropyl)benzonitrile (D91) (400 mg). MS (ES): C14H13BrN2S requires 320. found 321.0 (M+H+).

후처리

  1. customThe reaction mixture was sealed
  2. temperatureheated under microwave at 120° C. for 4 h
  3. temperatureAfter cooling
  4. customthe reaction
  5. filtrationfiltered through silical 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. customThe solvent was removed in vacuo
  10. customto give the crude product, which
  11. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-d1bda75ef4b146228af169e4257fb575
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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