Trimethylsilylacetylene → 5-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine

HRID 1515845

反応式

HRID 1515845 の反応式
[NH2:1][C:2]1[C:7](I)=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>C(N(CC)CC)C.O1CCCC1.CN(C)C(=O)C.[Cu]I.C1(P([Pd-](Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:9]([C:5]1[CH:6]=[C:7]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[C:2]([NH2:1])=[N:3][CH:4]=1)([O-:11])=[O:10]

参加物

8

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 116231122-Amino-3-iodo-5-nitropyridine

生成物 1

HCID 115287895-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine収率 70%

試薬・触媒・溶媒 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178479804HCID 178479804、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 31374Dimethylacetamide溶媒

実験手順

2-Amino-3-iodo-5-nitropyridine (10.0 g, 37.75 mmol) was dissolved in a mixture of triethylamine (250 mL), tetrahydrofuran (40 mL), N,N-dimethylacetamide (80 mL) and the solution was degassed and purged with nitrogen. Trimethylsilylacetylene (8.0 mL, 56.5 mmol), copper(I) iodide (0.145 g, 0.75 mmol) and bis(triphenylphosphino) palladium (II) chloride (0.53 g, 0.75 mmol) were added. The mixture was degassed and purged with nitrogen one more time, then stirred at ambient temperature for 16 h. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 15%-35% ethyl acetate/hexanes) to afford 5-nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine (6.2 g, 70%) as a yellow solid: LC/MS m/e calcd for C10H13N3O2Si [M+H]+ 236.32, observed 236.0.

後処理

  1. customthe solution was degassed
  2. custompurged with nitrogen
  3. customThe mixture was degassed
  4. custompurged with nitrogen one more time
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 15%-35% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-d69067af30874b68b609adb255ea63d3
出典データセット
uspto-grants-2012_07
特許番号
US08222416B2

関連ノート

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