Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane → (4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester

HRID 853096노트

반응식

HRID 853096 반응식
[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1I.[CH3:15][Si:16]([CH3:27])([O:23][CH2:24][C:25]#[CH:26])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]>C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:14])[NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:6]=1[C:26]#[C:25][CH2:24][O:23][Si:16]([CH3:27])([CH3:15])[C:17]([CH3:22])([CH3:21])[CH:18]([CH3:20])[CH3:19]

참가 물질

4

반응물 2

HCID 18455989Dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silaneHCID 57543475Methyl (4-Bromo-2-iodo-5-methylphenyl)carbamate

생성물 1

HCID 68890098(4-Bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester수율 43.6%

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

To a solution of 3.70 g (4-bromo-2-iodo-5-methyl-phenyl)-carbamic acid methyl ester and 0.070 g bis-triphenylphosphine palladium dichloride and 0.038 g cuprous iodide in 25 ml triethylamine was added 2.38 g dimethyl (2-propynyloxy)(1,1,2-trimethylpropyl)-silane and the mixture was heated 2 h at reflux. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine, dried with magnesium sulfate and purified by chromatography on silica gel with hexane:ethyl acetate=4:1 to yield 1.92 g (4-bromo-2-{3-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-prop-1-ynyl}-5-methyl-phenyl)-carbamic acid methyl ester as a light brown oil. MS: M+NH4+=457.0 M+Na+=462.2

후처리

  1. temperaturethe mixture was heated 2 h
  2. temperatureat reflux
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. washthe organic phase was washed with 1N hydrochloric acid, sodium bicarbonate and brine
  6. dry with materialdried with magnesium sulfate
  7. custompurified by chromatography on silica gel with hexane

출처 및 근거

ORD 기록
ord-3822e9602b8a4b2c88b8a9bcde58ab84
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253281B2

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