Tetrahydrofuran → 5-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

HRID 877934

반응식

HRID 877934 반응식
[Cl:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH2:8])=[N:6][CH:7]=1.C1COCC1.C(N(CC)CC)C.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24]>[Cu](I)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(OCC)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:27]#[C:26][Si:23]([CH3:25])([CH3:24])[CH3:22])[C:5]([NH2:8])=[N:6][CH:7]=1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 110760102-Amino-5-chloro-3-iodopyridine

생성물 1

HCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine수율 100%

시약·촉매·용매 3

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매

실험 절차

A 250 ml round bottom flask was charged with 5-chloro-3-iodo-pyridin-2-ylamine (1) (42 g, 165 mmol), THF (100 ml), copper iodide (315 mg, 1.65 mmol) and PdCl2(PPh3)2 (1.15 g, 1.65 mmol) under nitrogen. Triethylamine (70 ml, 0.5 mol), and trimethylsilyl acetylene (30 ml, 0.21 mol). The reaction mixture was stirred at room temperature for 2 h. The reaction mixture was then cooled to 0° C. and diethyl ether was added. The suspension was filtered through a celite and thoroughly washed with diethyl ether. The filtrate was concentrated and pre-absorbed onto silica gel and purified by column chromatography using as eluent, pentane/DCM 10% to 100%, to afford an off white solid (36 g, 100%). 1H NMR (CDCl3): 0.3 (9H, s), 5.0-5.1 (2H, brs), 7.6 (1H, s), 7.9 (1H, s). MS (ES+): 225, 227.

후처리

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. filtrationThe suspension was filtered through a celite
  3. washthoroughly washed with diethyl ether
  4. concentrationThe filtrate was concentrated
  5. custompre-absorbed onto silica gel
  6. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-5292a353f2e74185b23442072508ad1e
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987454B2

연결된 노트

불러오는 중…