Trimethylsilylacetylene → (2-Trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester

HRID 400606

반응식

HRID 400606 반응식
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[C:9](Br)=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.CN(C=O)C.C(OCC)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>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[C:9]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 14177127(2-Bromo-Pyridin-3-Yl)-Carbamic Acid Tert-Butyl Ester

생성물 1

HCID 60026792(2-Trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester수율 43%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

실험 절차

A mixture of (2-bromopyridin-3-yl)carbamic acid tert-butyl ester (1.09 mg, 4.00 mmol), (trimethylsilyl)acetylene (2.83 mL, 20.0 mmol), CuI (75.8 mg, 0.400 mmol), and dichlorobis(triphenylphosphine)palladium (II) (141 mg, 0.200 mmol) in a mixture of 12 mL of triethylamine and 3.0 mL of anhydrous DMF were stirred at room temperature overnight. The reaction was diluted with 50 mL of diethyl ether and quenched with 50 mL of saturated aqueous ammonium chloride solution. The organic layer was washed with 20 mL of saturated aqueous ammonium chloride solution and the combined aqueous layers were extracted with three 20 mL portions of diethyl ether. The combined organic layers were then washed with 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (20% to 30% ethyl acetate in hexanes, gradient) gave 500 mg of (2-trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester (43% yield).

후처리

  1. customquenched with 50 mL of saturated aqueous ammonium chloride solution
  2. washThe organic layer was washed with 20 mL of saturated aqueous ammonium chloride solution
  3. extractionthe combined aqueous layers were extracted with three 20 mL portions of diethyl ether
  4. washThe combined organic layers were then washed with 20 mL of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-fdfca58b42664c359b988642b9bb1c62
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741897B2

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