Benzene, 1-chloro-4-ethynyl- → HCID 71255724, 화합물

HRID 2202148노트

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HRID 2202148 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:18]([CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]1)=[O:19]>C1COCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:18]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[O:19])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 70118Benzene, 1-chloro-4-ethynyl-HCID 11065582tert-Butyl 4-(methoxy(methyl)carbamoyl)piperidine-1-carboxylate2회HCID 178418339Butyllithium

생성물 1

HCID 71255724HCID 71255724, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 1-chloro-4-ethynylbenzene (2.76 g, 20.20 mmol) in THF (50 mL) at −78° C. was added 2.5 M butyllitium (8.81 ml, 22.03 mmol in hexane) and stirred for 1 h at −78° C. tert-Butyl 4-[methoxy(methyl)carbamoyl]piperidine-1-carboxylate (Compound 1.2, 5 g, 18.36 mmol) was added. The mixture was stirred at −78° C. for 30 min, then warmed up to 0° C., stirred for another hour at the same temperature, and diluted with water. The organic layer was separated and the aqueous was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, and the drying agent was filtered off. The filtrate was concentrated. The residue was purified by silica gel column chromatography using gradient elution (5 to 30%, EtOAc/hexane). LC-MS m/z 292.06 [M−56+H]+.

후처리

  1. additionwas added
  2. temperaturewarmed up to 0° C.
  3. stirringstirred for another hour at the same temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with ethyl acetate
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationthe drying agent was filtered off
  8. concentrationThe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography
  10. washelution (5 to 30%, EtOAc/hexane)

출처 및 근거

ORD 기록
ord-48e75d6d8e704b53aeabf7cef64777ea
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365539B2

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