Trimethylsilylacetylene → Methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate

HRID 2053763ノート

反応式

HRID 2053763 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:19][Si:20]([C:23]#[CH:24])([CH3:22])[CH3:21]>C(NC(C)C)(C)C.C(OCC)(=O)C.[Cu]I>[N:14]1([C:12]([C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])=[O:13])[CH2:18][CH2:17][CH2:16][CH2:15]1

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 69312594Methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate

生成物 1

HCID 69309966Methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 7912Diisopropylamine溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

18 g (57.7 mmol) of methyl 3-bromo-4-(pyrrolidin-1-ylcarbonyl)benzoate is placed under a nitrogen atmosphere together with 6.66 g (5.77 mmol) of tetrakis-triphenylphosphinepalladium(0) and 0.439 g (2.31 mmol) of copper(1) iodide in 150 mL of N,N-diisopropylamine, the mixture is heated to 80° C. and 16.6 mL (115 mmol) trimethylsilylethyne is added. The reaction mixture is stirred for 8 hours at 80° C. and then for 16 hours at ambient temperature. Then volatile constituents are eliminated in vacuo, the residue is taken up in ethyl acetate, insoluble matter is filtered off, and the solvent is eliminated in vacuo. The residue is purified by chromatography on silica gel (gradient: dichloromethane/ethanol 100:0□95:5). Yield: 7.7 g (41%); Rf value: 0.44 (silica gel; dichloromethane/ethanol=95:5); C18H23NO3Si (329.48); mass spectrum: (M+H)+=330.

後処理

  1. waitfor 16 hours at ambient temperature
  2. filtrationinsoluble matter is filtered off
  3. customThe residue is purified by chromatography on silica gel (gradient: dichloromethane/ethanol 100:0□95:5)

出典と根拠

ORDレコード
ord-9ecb5fa6c4f840b19b9f70e14d54589a
出典データセット
uspto-grants-2008_02
特許番号
US07326791B2

反応ノート

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