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Potassium Carbonate → 1,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate

HRID 564568
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인쇄 미리보기

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HRID 564568 반응식
Br[C:2]1[CH:3]=[C:4]([CH:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:5]=[CH:6][CH:7]=1.[C:22]([C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)#[N:23].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[C:22]([C:24]1[CH:29]=[C:28]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[C:9]3[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]3)[CH:3]=2)[CH:27]=[CH:26][CH:25]=1)#[N:23]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 27343253-Cyanophenylboronic acidHCID 57813409Tert-butyl 4-(3-bromobenzylidene)piperidine-1-carboxylate

생성물 1

HCID 670058691,1-Dimethylethyl 4-[(3'-cyano-3-biphenylyl)methylidene]-1-piperidinecarboxylate수율 85.4%

시약·촉매·용매 2

HCID 962Water용매
HCID 31275
1,4-Dioxane
용매

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온도
130 °C

실험 절차

To a solution of 1,1-dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate (2.07 g, 5.88 mmol) in p-dioxane (30 mL) and H2O (10 mL) was added (3-cyanophenyl)boronic acid (1.036 g, 7.05 mmol), Pd(PPh3) (0.272 g, 0.235 mmol), and K2CO3 (2.436 g, 17.63 mmol) and then the reaction was heated in a microwave at 130° C. for 15 minutes. The organic layer of the reaction mixture was separated, concentrated and purified by Combiflash chromatograph to afford 1.88 g (85%) of the title compound. LC-MS m/z 749 (2M+H)+.

후처리

  1. customThe organic layer of the reaction mixture was separated
  2. concentrationconcentrated
  3. custompurified by Combiflash chromatograph

출처 및 근거

ORD 기록
ord-a05dac54005349b08cf1ad8f9d50ee1c
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067408B2

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