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

HRID 877934

反応式

HRID 877934 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5292a353f2e74185b23442072508ad1e
出典データセット
uspto-grants-2015_03
特許番号
US08987454B2

関連ノート

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