Triethylamine → 3-Nitro-2-vinylpyridine

HRID 629191노트

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HRID 629191 반응식
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[B-](F)(F)(F)[CH:12]=[CH2:13].[K+].C(N(CC)CC)C>C(O)(C)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[N+:8]([C:7]1[C:2]([CH:12]=[CH2:13])=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 796132-Chloro-3-nitropyridineHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 118296173-Nitro-2-vinylpyridine수율 52.8%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 3776Isopropanol용매

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온도
100 °C

실험 절차

A solution of 2-chloro-3-nitropyridine (0.20 g, 1.261 mmol), potassium trifluoro(vinyl)borate (0.203 g, 1.514 mmol) and PdCl2(dppf) (0.018 g, 0.025 mmol) dissolved in isopropanol (4 mL) and triethylamine (0.211 mL, 1.514 mmol) was gently purged with stream of nitrogen for a few minutes then heated at 100° C. for 4 h. The reaction was cooled and filtered through CELITE® and the solvent was removed under vacuum. The resulting residue was purified via automated flash chromatography (40 gram silica gel, hex/ethyl acetate). Fractions containing the desired product were collected, combined, and evaporated in vacuo to afford tan oil as final product, 3-nitro-2-vinylpyridine (100 mg, 0.666 mmol, 52.8% yield). HPLC RT (Method N)=1.75 minutes.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through CELITE®
  3. customthe solvent was removed under vacuum
  4. customThe resulting residue was purified
  5. additionFractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-45a867ebb3d44c2c931dd8009d701aa4
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315494B2

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