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

HRID 1515845

반응식

HRID 1515845 반응식
[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]

참가 물질

8

반응물 2

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

생성물 1

HCID 115287895-Nitro-3-trimethylsilanylethynyl-pyridin-2-ylamine수율 70%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178479804HCID 178479804, 화합물촉매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매HCID 31374Dimethylacetamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d69067af30874b68b609adb255ea63d3
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08222416B2

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