Potassium Fluoride → HCID 178428567, 화합물

HRID 1748534노트

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HRID 1748534 반응식
[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:22])=[CH:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F-].[K+]>O1CCCC1.O.C(OCC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Si:1]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[N:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH3:22])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

참가 물질

7

반응물 2

HCID 522689Potassium FluorideHCID 866924826-(4-{[tert-Butyl(dimethyl)silyl]oxy}cyclohex-1-en-1-yl)-5-methylpyridin-3-amine

생성물 1

HCID 178428567HCID 178428567, 화합물수율 89.4%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-(4-{[tert-butyl(dimethyl)silyl]oxy}-cyclohex-1-en-1-yl)-5-methylpyridin-3-amine (1.5 g) described in Reference Example 110, palladium acetate (211 mg) and potassium fluoride (1.09 g) in tetrahydrofuran (24 ml) and water (10 ml) was slowly added dropwise polymethylhydrosiloxane (PMHS) (1.12 ml) at room temperature with stirring, and then stirred at room temperature for 2 hours. After completion of the reaction, the reaction solution was diluted with diethyl ether, filtered through Celite, and then the filtrate was concentrated to half of the volume. Then, saturated brine was added thereto, the mixture was extracted with ethyl acetate, the obtained organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated in vacuo. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give the titled compound (1.35 g) as a light brown solid. MS (ESI) m/z: 321 (M+H)+.

후처리

  1. stirringstirred at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. filtrationfiltered through Celite
  4. concentrationthe filtrate was concentrated to half of the volume
  5. additionThen, saturated brine was added
  6. extractionthe mixture was extracted with ethyl acetate
  7. dry with materialthe obtained organic layer was dried over anhydrous sodium sulfate
  8. customthe solvent was evaporated in vacuo
  9. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

출처 및 근거

ORD 기록
ord-b673e6b9d9144747a5695e2f91f0bcce
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09150555B2

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