Diisopropylamine → 2-(2-Fluoropyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]ethanone

HRID 862207노트

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HRID 862207 반응식
C(NC(C)C)(C)C.C([Li])CCC.[F:13][C:14]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][N:15]=1.CON(C)[C:24](=[O:35])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1>C1COCC1>[F:13][C:14]1[CH:19]=[C:18]([CH2:20][C:24]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=2)=[O:35])[CH:17]=[CH:16][N:15]=1

참가 물질

6

반응물 4

HCID 7912DiisopropylamineHCID 27374032-Fluoro-4-methylpyridineHCID 14069349N-Methoxy-N-methyl-3-(trifluoromethyl)benzamideHCID 178418339Butyllithium

생성물 1

HCID 119771402-(2-Fluoropyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]ethanone수율 84.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
-78 °C

실험 절차

To a solution of diisopropylamine (17.69 mL, 0.135 mole) in THF (200 mL) at -78° C., under argon, was added n-butyllithium (54.0 mL, 2.5M in hexane, 0.135 mole), followed after 5 min. by a solution of 2-fluoro-4-methylpyridine (Lancaster Synthesis Inc.) (10 g, 0.090 mole) in THF (20 mL). After stirring for 15 min. at -78° C., a solution of N-methoxy-N-methyl-3-trifluoromethylbenzamide (23.08 g, 0.099 mole) in THF (10 mL) was added. After stirring for 5 min, the reaction was allowed to warm to 0° C. and quenched by pouring into water (400 mL) and ethyl acetate (400 mL). The layers were separated, and the aqueous layer washed with ethyl acetate (200 mL). The ethyl acetate extracts were combined, dried over anhydrous sodium sulfate, filtered, and concentrated to an oil which was chromatographed on silica gel with 20% ethyl acetate in hexane to give 21.6 g of the title compound.

후처리

  1. stirringAfter stirring for 5 min
  2. temperatureto warm to 0° C.
  3. customquenched
  4. additionby pouring into water (400 mL) and ethyl acetate (400 mL)
  5. customThe layers were separated
  6. washthe aqueous layer washed with ethyl acetate (200 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated to an oil which
  10. customwas chromatographed on silica gel with 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-ec63435d504f4ca5bbd7ab94805ca4f9
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05717100

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