Ethanol → Piperidine, 1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-4-(phenyl-2-pyridinylmethylene)-

HRID 606735노트

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HRID 606735 반응식
Br[C:2](=[C:9]1[CH2:14][CH2:13][N:12]([C:15](=[O:31])[C:16]([C:18]2[C:26]3[C:21](=[C:22]([O:29][CH3:30])[N:23]=[CH:24][C:25]=3[O:27][CH3:28])[NH:20][CH:19]=2)=[O:17])[CH2:11][CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34](B(O)O)[CH:33]=1.C(=O)([O-])[O-].[Na+].[Na+].CCO>COCCOC>[C:3]1([C:2](=[C:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:31])[C:16]([C:18]3[C:26]4[C:21](=[C:22]([O:29][CH3:30])[N:23]=[CH:24][C:25]=4[O:27][CH3:28])[NH:20][CH:19]=3)=[O:17])[CH2:11][CH2:10]2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][N:32]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 5279817Piperidine, 4-(bromophenylmethylene)-1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-

생성물 1

HCID 5279859Piperidine, 1-[2-(4,7-dimethoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-1,2-dioxoethyl]-4-(phenyl-2-pyridinylmethylene)-수율 37%

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

To a solution of 1-[4-(1-bromo-1-phenyl-methylene)-piperidin-1-yl]-2-(4,7-dimethoxy-6-azaindol-3-yl)-ethane-1,2-dione (0.030 g, 0.062 mmole), pyridine-3-boronic acid (0.011 g, 0.093 mmol) in 4 mL of DME was added 2M sodium carbonate (0.12 mL, 0.24 mmol) and EtOH (1 mL) and the resulting mixture was degassed with a stream of Ar bubbles for 10 min. To this mixture was added Pd(dppf)2Cl2 (0.003 g, 5 mol %) and the reaction mixture was heated with stirring at 90° C. for 18 h. The cooled mixture was then filtered (C-18 cartridge and 0.45 μm filter), the residue was washed with MeOH and the filtrate was evaporated. Purification of the residual material by preparative HPLC afforded the title compound (0.011 g, 37%) as a light gray solid:

후처리

  1. customthe resulting mixture was degassed with a stream of Ar bubbles for 10 min
  2. additionTo this mixture was added Pd(dppf)2Cl2 (0.003 g, 5 mol %)
  3. temperaturethe reaction mixture was heated
  4. filtrationThe cooled mixture was then filtered
  5. filtration(C-18 cartridge and 0.45 μm filter)
  6. washthe residue was washed with MeOH
  7. customthe filtrate was evaporated
  8. customPurification of the residual material by preparative HPLC

출처 및 근거

ORD 기록
ord-17e78b23bd5d4d709bd5c5ab51c2e94f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915283B2

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