Water → 2-Isopropoxy-5-thiazol-2-ylbenzonitrile

HRID 1942636노트

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HRID 1942636 반응식
[CH3:1][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10](B2OC(C)(C)C(C)(C)O2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:3].Br[C:23]1[S:24][CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.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>[CH3:3][CH:2]([O:4][C:5]1[CH:12]=[CH:11][C:10]([C:23]2[S:24][CH:25]=[CH:26][N:27]=2)=[CH:9][C:6]=1[C:7]#[N:8])[CH3:1]

참가 물질

8

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 764302-BromothiazoleHCID 575060272-Isopropoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

생성물 1

HCID 575060282-Isopropoxy-5-thiazol-2-ylbenzonitrile수율 53.9%

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

To a suspension of 2-[(1-methylethyl)oxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (D39) (109 mg), 2-bromo-1,3-thiazole (93 mg) and cesium carbonate (148 mg) in acetonitrile (3 mL)/water (0.750 mL) stirred under nitrogen was added PdCl2(dppf)-CH2Cl2 adduct (31.0 mg). The reaction vessel was sealed and heated under microwave at 120° C. for 1 h. After cooling the reaction, the reaction mixture was diluted with ethyl acetate, filtered through celite. The filtrate was partitioned between ethyl acetate and water. The organic phase was dried over sodium sulphate and evaporated in vacuo to give the crude product, which was purified by column chromatography to afford 2-[(1-methylethyl)oxy]-5-(1,3-thiazol-2-yl)benzonitrile (D64) (50 mg). MS (ES): C13H12N2OS requires 244. found 245.1 (M+H+).

후처리

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe reaction
  4. filtrationfiltered through celite
  5. customThe filtrate was partitioned between ethyl acetate and water
  6. dry with materialThe organic phase was dried over sodium sulphate
  7. customevaporated in vacuo
  8. customto give the crude product, which
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-e977d882c7644fb3b83bd450bb46b14b
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389508B2

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