Triethylamine → 3-Nitro-2-vinylpyridine

HRID 629191ノート

反応式

HRID 629191 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 118296173-Nitro-2-vinylpyridine収率 52.8%

試薬・触媒・溶媒 2

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-45a867ebb3d44c2c931dd8009d701aa4
出典データセット
uspto-grants-2016_04
特許番号
US09315494B2

反応ノート

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