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Sodium Iodide → HCID 18381962, 화합물

HRID 751516
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HRID 751516 반응식
C[Si](Cl)(C)C.[I-].[Na+].[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH:30](O)[C:31]([NH2:33])=[O:32])=[CH:22]2)[CH2:17][CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(#N)C>[CH2:8]([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]([CH2:30][C:31]([NH2:33])=[O:32])=[CH:22]2)[CH2:17][CH2:16]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
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참가 물질

5

반응물 3

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 69269014HCID 69269014, 화합물

생성물 1

HCID 18381962HCID 18381962, 화합물수율 67%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
0 °C

실험 절차

Dissolve trimethylsilyl chloride (2.1 mL, 6 eq) and sodium iodide (2.5 g, 6 eq) in acetronitrile (15 mL) and cool to 0° C. while under nitrogen. Dissolve 2-[1-(1-benzylpiperidin-4-yl)-1H-indol-3-yl]-2-hydroxyacetamide (1.0 g, 2.75 mmol) in acetonitrile (10 mL) and add dropwise to the reaction. Let stir overnight and gradually warm to room temperature. Extract with 5% NaHSO3 against ethyl acetate then wash with brine. Basify aqueous layer with saturated sodium bicarbonate and wash with ethyl acetate once more. Combine organic layers and dry over magnesium sulfate. Filter and concentrate. Triturate from hot diethyl ether to afford product (0.64 g, 67%) as a white solid. MS (ES, m/z): 348.0 (M+1).

후처리

  1. temperaturegradually warm to room temperature
  2. extractionExtract with 5% NaHSO3 against ethyl acetate
  3. washthen wash with brine
  4. washBasify aqueous layer with saturated sodium bicarbonate and wash with ethyl acetate once more
  5. dry with materialCombine organic layers and dry over magnesium sulfate
  6. filtrationFilter
  7. concentrationconcentrate
  8. customTriturate from hot diethyl ether

출처 및 근거

ORD 기록
ord-c8482bd0d6ea4bf894dbcfb07c78d42b
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07405305B2

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