Triethylamine → (2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

HRID 2080014ノート

反応式

HRID 2080014 の反応式
[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[C:7](Br)=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2].C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>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.[Cu]I.O>[CH2:1]([O:3][C:4](=[O:13])[NH:5][C:6]1[C:7]([C:26]#[C:25][Si:22]([CH3:24])([CH3:23])[CH3:21])=[N:8][CH:9]=[CH:10][CH:11]=1)[CH3:2]

参加物

7

反応物 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 13803673(2-Bromo-pyridin-3-yl)carbamic acid ethyl ester

生成物 1

HCID 58875356(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of (2-bromo-pyridin-3-yl)carbamic acid ethyl ester described in Preparation Example S-2 (395 mg, 1.6 mmol), dichlorobis(triphenylphosphine)palladium(II) (20 mg, 0.028 mmol), triethylamine (0.25 mL, 1.8 mmol), copper(I)iodide (10 mg, 0.05 mmol) and trimethylsilylacetylene (0.131 mL, 2.4 mmol) was placed in a sealed tube, and heated at 100° C. for 4 hours. After the reaction was completed, the reaction mixture was poured into water, which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2), and the title compound (0.42 g, 1.6 mmol, quantitatively) was obtained.

後処理

  1. customwas placed in a sealed tube
  2. extractionwas then extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)

出典と根拠

ORDレコード
ord-38b66cdb980e43b8bfa2ab56c26bf236
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

反応ノート

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