Lithium Hexamethyldisilazide → 2-(3,5-Dichloro-pyridin-4-yl)-1-(4-methoxy-8-nitro-dibenzo-furan-1-yl)-ethanone

HRID 2427857

반응식

HRID 2427857 반응식
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:20][O:21][C:22]1[C:27]2[O:28][C:29]3[CH:34]=[CH:33][C:32]([N+:35]([O-:37])=[O:36])=[CH:31][C:30]=3[C:26]=2[C:25]([C:38](Cl)=[O:39])=[CH:24][CH:23]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:9])[C:7]=1[CH2:8][C:38]([C:25]1[C:26]2[C:30]3[CH:31]=[C:32]([N+:35]([O-:37])=[O:36])[CH:33]=[CH:34][C:29]=3[O:28][C:27]=2[C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)=[O:39]

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 109538273,5-Dichloro-4-methylpyridineHCID 860058584-Methoxy-8-nitro-dibenzofuran-1-carbonyl chloride

생성물 1

HCID 671482962-(3,5-Dichloro-pyridin-4-yl)-1-(4-methoxy-8-nitro-dibenzo-furan-1-yl)-ethanone수율 32.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-60 °C

실험 절차

A solution of 3,5-dichloro-4-methyl-pyridine (0.593 g, 3.66 mmoles) in tetrahydrofuran (200 mL) is cooled to −60° C. under nitrogen atmosphere. A 1M solution of lithium bis(trimethylsilyl) amide (4.4 mL, 4.4 mmoles) is added dropwise and the resulting mixture is stirred at −60° C. for 30 minutes. A solution of 4-methoxy-8-nitro-dibenzofuran-1-carbonyl chloride (3a) (0.75 g, 2.44 mmoles) in dry tetrahydrofuran (20 mL) is added dropwise, maintaining the temperature below −60° C. After stirring for 15 minutes at −60° C., the mixture is stirred at room temperature for 3.5 hours. The mixture is then quenched with a saturated NH4Cl solution (20 mL); the product precipitated as a solid which is recovered by filtration and washed with methanol to yield 340 mg of the title compound.

후처리

  1. temperaturemaintaining the temperature below −60° C
  2. stirringAfter stirring for 15 minutes at −60° C.
  3. stirringthe mixture is stirred at room temperature for 3.5 hours
  4. customThe mixture is then quenched with a saturated NH4Cl solution (20 mL)
  5. customthe product precipitated as a solid which
  6. filtrationis recovered by filtration
  7. washwashed with methanol

출처 및 근거

ORD 기록
ord-0f7d5c369b52429c9bd9f24cb6b21a6e
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07968724B2

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