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

HRID 400606

反応式

HRID 400606 の反応式
[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]

参加物

8

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fdfca58b42664c359b988642b9bb1c62
出典データセット
uspto-grants-2014_06
特許番号
US08741897B2

関連ノート

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