Water → Tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate

HRID 1465430노트

반응식

HRID 1465430 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:27]([Si:29]([CH3:32])([CH3:31])[CH3:30])#[CH:28].O>CN(C)C=O.[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>[CH3:30][Si:29]([C:27]#[C:28][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:10])=[CH:4][CH:3]=1)([CH3:32])[CH3:31]

참가 물질

8

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 67029623Tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate

생성물 1

HCID 67266446Tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate수율 68%

시약·촉매·용매 3

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

반응 조건

온도
50 °C

실험 절차

To a solution of tert-butyl 2-[(4-bromophenyl)acetyl]hydrazinecarboxylate (10 g, 30.4 mmol), copper (I) iodide (579 mg, 3.04 mmol), dichlorobis(triphenylphosphine)palladium (II) (2.13 g, 3.03 mmol) and triethylamine (8.5 ml, 61.0 mmol) in anhydrous N,N-dimethylformamide (50 ml) was added ethynyltrimethylsilane (6.3 ml, 45.5 mmol). After stirring overnight at 50° C., water was added to the reaction mixture, and the mixture was extracted with ethyl acetate and concentrated under reduced pressure. The concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70→35:65) to give tert-butyl 2-({4-[(trimethylsilyl)ethynyl]phenyl}acetyl)hydrazinecarboxylate (7.1 g, yield 68%) as a greeny brown solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationconcentrated under reduced pressure
  3. customThe concentrated residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70→35:65)

출처 및 근거

ORD 기록
ord-76a62d6438494e5f8cf6fee8a7be0abd
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999989B2

반응 노트

불러오는 중…