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

HRID 606735Notes

Reaction equation

HRID 606735 reaction equation
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

Participants

6

Reactant 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]-

Product 1

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

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

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:

Workup

  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

Sources & evidence

ORD record
ord-17e78b23bd5d4d709bd5c5ab51c2e94f
Source dataset
uspto-grants-2011_03
Patent number
US07915283B2

Reaction notes

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