Potassium Carbonate → 4-Bromo-3,5-dimethylphenyl 3-(pyridin-3-yl)propiolate

HRID 1483196ノート

反応式

HRID 1483196 の反応式
I[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].[C:14]([O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([Br:26])=[C:21]([CH3:27])[CH:20]=1)(=[O:17])[C:15]#[CH:16]>C1COCC1.[Cu]I>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:16]#[C:15][C:14]([O:18][C:19]2[CH:20]=[C:21]([CH3:27])[C:22]([Br:26])=[C:23]([CH3:25])[CH:24]=2)=[O:17])[CH:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 707143-IodopyridineHCID 725452334-Bromo-3,5-dimethylphenyl propiolate

生成物 1

HCID 894777664-Bromo-3,5-dimethylphenyl 3-(pyridin-3-yl)propiolate収率 27%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
65 °C

実験手順

3-Iodopyridine (226 mg, 1.10 mmol) in THF (2 mL) was degassed under reduced pressure at −78° C., and then nitrogen gas was introduced. To the solution was added K2CO3 (276 mg, 2.00 mmol), CuI (15 mg, 0.079 mmol) and PdCl2(Ph3P)2 (7 mg, 0.01 mmol), and the mixture was stirred at 65° C. 4-bromo-3,5-dimethylphenyl propiolate (6-1) (253 mg, 1.00 mmol) in THF (2 mL) was added by syringe pump over a period of 5 h, and the mixture was stirred an additional 1 h after addition was complete. After being cooled to room temperature, the mixture was filtered. The filtrate was concentrated and purified by silica gel column chromatography to give the title compound 13-1 (88 mg, 27% yield) as a black oil.

後処理

  1. additionnitrogen gas was introduced
  2. stirringthe mixture was stirred an additional 1 h
  3. additionafter addition
  4. temperatureAfter being cooled to room temperature
  5. filtrationthe mixture was filtered
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography

出典と根拠

ORDレコード
ord-e69b31c53b6f440d89aed35f1d475339
出典データセット
uspto-grants-2016_08
特許番号
US09416121B2

反応ノート

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