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

HRID 2080014노트

반응식

HRID 2080014 반응식
[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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-38b66cdb980e43b8bfa2ab56c26bf236
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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