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

HRID 1483196노트

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HRID 1483196 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매2회

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온도
65 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e69b31c53b6f440d89aed35f1d475339
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09416121B2

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