Piperidine → HCID 71278508, compound

HRID 1749800Notes

Reaction equation

HRID 1749800 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[CH2:7][O:8][C:4]=2[C:3]=1[CH2:12][N:13]1[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][N:27]=2)[C:22]([CH:29]=O)=[CH:21]1.N1CCCCC1>C(O)(C)C>[NH:20]1[C:28]2=[N:27][CH:26]=[CH:25][CH:24]=[C:23]2[C:22](/[CH:29]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:18][CH2:17][NH:16][C:15](=[O:19])[CH2:14]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[CH:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 71278572HCID 71278572, compound

Product 1

HCID 71278508HCID 71278508, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent3×

Procedure

A solution of 4-[(6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl)methyl]piperazin-2-one (0.0986 g, 0.376 mmol) in isopropanol (1.5 mL) was added with 7-aza-1H-indole-3-carboxaldehyde (0.0550 g, 0.376 mmol) and piperidine (0.00320 g, 0.0376 mmol), and the mixture was refluxed by heating for 2 hours. The reaction mixture was cooled to room temperature, and then added with isopropanol (2 mL), and the precipitated solid was suspended in isopropanol and thereby washed. The solid was collected by filtration to obtain the objective (Z)-4-({2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)piperazin-2-one (0.106 g, 72%).

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 2 hours
  3. washwashed
  4. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-7e08072645fa4ab5afb06c4064de6d77
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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