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

HRID 592356노트

반응식

HRID 592356 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

  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.)

출처 및 근거

ORD 기록
ord-d60519605f4f4474a60e4e6da7644cdf
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238644B2

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