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HRID724726

反应详情

EQUATION

反应方程式

HRID 724726 的结构方程式

REACTANTS

反应物

4
结构：CN(C)C=O
HCID6228

N,N-Dimethylformamide

C3H7NO

结构：CCN(CC)CC
HCID8471

Triethylamine

C6H15N

结构：CC(C)(C)N1C(=O)C=CS1(=O)=O
HCID11116816

未命名化合物

结构：CC(C)(C)OC(=O)N[C@@H](Cc1ccc(I)c(Br)c1)c1ncc(-c2ccccc2)n1COCC[Si](C)(C)C
HCID58746876

未命名化合物

PRODUCTS

生成物

1
结构：CC(C)(C)OC(=O)N[C@@H](Cc1ccc(C2=CC(=O)N(C(C)(C)C)S2(=O)=O)c(Br)c1)c1ncc(-c2ccccc2)n1COCC[Si](C)(C)C
HCID58746634

未命名化合物

收率 24%

AUXILIARIES

试剂、催化剂与溶剂

3
结构：CCCC[N+](CCCC)(CCCC)CCCC.[Cl-]
催化剂HCID70681

未命名化合物

结构：CC(=O)[O-].CC(=O)[O-].[Pd+2]
催化剂HCID167845

Diacetatopalladium

C4H6O4Pd

结构：O
溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度
70 °C

PROCEDURE

实验过程

A solution of tert-butyl [(1S)-2-(3-bromo-4-iodophenyl)-1-(5-phenyl-1-[2-(trimethylsilyl)ethoxy]methyl-1H-imidazol-2-yl)ethyl]carbamate (130 mg, 112 μmol), 2-tert-butylisothiazol-3(2H)-one 1,1-dioxide (42.3 mg, 223 μmol), triethylamine (46.7 mL, 335 μmol), palladium acetate (25.1 mg, 112 μmol), N,N-dimethylformamide (3.0 mL) and tetra-N-butylammonium chloride (31.0 mg, 112 μmol) was degassed and stirred at 70° C. for 2 h. The reaction was diluted with water and extracted with ethyl acetate three times, dried with sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by flash column chromatography to yield the desired product (20.0 mg, 24%). MF=C35H47BrN4O6SSi; LCMS found for C35H48BrN4O6SSi (M+H)+: m/z=759.

WORKUP

后处理

  1. extractionextracted with ethyl acetate three times
  2. dry with materialdried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by flash column chromatography