Trimethylsilylacetylene → 2-(2-((Trimethylsilyl)ethynyl)phenyl)propanamide

HRID 592356ノート

反応式

HRID 592356 の反応式
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH3:31][Si:32]([C:35]#[CH:36])([CH3:34])[CH3:33]>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:31][Si:32]([C:35]#[C:36][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH3:12])[C:9]([NH2:11])=[O:10])([CH3:34])[CH3:33]

参加物

7

反応物 3

HCID 66111TrimethylsilylacetyleneHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 867122772-(2-Iodophenyl)propanamide

生成物 1

HCID 867122802-(2-((Trimethylsilyl)ethynyl)phenyl)propanamide

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A mixture of 2-(2-iodophenyl)propanamide I13 (16.5 g, 0.060 mol), CuI (0.229 g, 1.20 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.348 g, 1.20 mmol), PdCl2(PPh3)2 (0.421 g, 0.600 mmol) and trimethylsilylacetylene (10.3 mL, 0.072 mol) in DMF (60 mL) was bubbled with N2 for 10 minutes. Et3N (50 mL) was then added and the mixture was stirred under nitrogen at 60° C. for 5 hours. The reaction mixture was cooled and the volatiles were removed in vacuo. The dark brown residue was adsorbed onto silica and purified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.) to give the title compound I15 as an orange oil (11.5 g, 78%). LCMS-D: rt 3.49 min; m/z 246 [M+H]+.

後処理

  1. customwas bubbled with N2 for 10 minutes
  2. additionEt3N (50 mL) was then added
  3. temperatureThe reaction mixture was cooled
  4. customthe volatiles were removed in vacuo
  5. custompurified by column chromatography (Biotage Isolera, 120 g SiO2 cartridge, 0-30% EtOAc in petroleum benzine 40-60° C.)

出典と根拠

ORDレコード
ord-d60519605f4f4474a60e4e6da7644cdf
出典データセット
uspto-grants-2016_01
特許番号
US09238644B2

反応ノート

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