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

HRID 606735ノート

反応式

HRID 606735 の反応式
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

参加物

6

反応物 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]-

生成物 1

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

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-17e78b23bd5d4d709bd5c5ab51c2e94f
出典データセット
uspto-grants-2011_03
特許番号
US07915283B2

反応ノート

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