Water → 6-Methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine

HRID 640477

反応式

HRID 640477 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5](Br)=[CH:4][CH:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12].O1CCOCC1.O>[Cu]I.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.C(OCC)(=O)C>[CH3:8][C:6]1[N:7]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10]

参加物

8

反応物 4

HCID 962WaterHCID 312751,4-DioxaneHCID 66111TrimethylsilylacetyleneHCID 1706782-Pyridinamine, 5-bromo-6-methyl-

生成物 1

HCID 592552326-Methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine収率 68.5%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 6-amino-3-bromo-2-methylpyridine (200 mg, 1.0 mmol), trimethylsilylacetylene (0.22 mL, 1.6 mmol), copper (I) iodide (9.9 mg, 0.052 mmol), and 1,4-dioxane (1.5 mL) was added bis(triphenylphosphine)palladium (II) chloride (73 mg, 0.10 mmol), which was stirred under nitrogen atmosphere for 3 hours and 30 minutes at 100° C. The reaction mixture was allowed to room temperature, water was added to the reaction mixture at the same temperature, ethyl acetate was added, and the mixture was filtered through a Celite pad. The organic layer of the filtrate was separated and washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure, and the residue thus obtained was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (140 mg, 57%, purity: 86%).

後処理

  1. customwas allowed to room temperature
  2. additionwas added
  3. filtrationthe mixture was filtered through a Celite pad
  4. customThe organic layer of the filtrate was separated
  5. washwashed with saturated aqueous sodium chloride
  6. concentrationwas concentrated under a reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-4a4737664898482ca5c07efeed9c36d1
出典データセット
uspto-grants-2010_04
特許番号
US07691882B2

関連ノート

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