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Piperidine → (Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one

HRID 1749798
Notes
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Reaction equation

HRID 1749798 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][O:16][CH2:15][CH2:14]1.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][N:26]=2)[C:21]([CH:28]=O)=[CH:20]1.N1CCCCC1>CO>[NH:19]1[C:27]2=[N:26][CH:25]=[CH:24][CH:23]=[C:22]2[C:21](/[CH:28]=[C:7]2\[O:8][C:4]3[C:3]([CH2:12][N:13]4[CH2:18][CH2:17][O:16][CH2:15][CH2:14]4)=[C:2]([OH:1])[CH:11]=[CH:10][C:5]=3[C:6]\2=[O:9])=[CH:20]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8082PiperidineHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehydeHCID 712789376-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one

Product 1

HCID 71278656(Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-oneYield 52.3%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent
3×

Conditions

Temperature
60 °C

Procedure

A solution of 6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.170 g, 0.684 mmol) obtained in Example A41, Step 1 in methanol (3 mL) was added with 7-aza-1H-indole-3-carboxaldehyde (0.100 g, 0.684 mmol) and piperidine (0.00582 g, 0.0684 mmol), and the mixture was stirred at 60° C. for 1 hour. The reaction mixture was cooled to room temperature, and then added with methanol (2 mL), and the precipitated solid was suspended in methanol and thereby washed. The solid was collected by filtration to obtain the objective (Z)-2-[(1H-pyrrolo[2,3-b]pyridin-3-yl)methylene]-6-hydroxy-7-(morpholinomethyl)benzofuran-3(2H)-one (0.135 g, 52%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed
  3. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-83bc6d5f5f2849309c4cdce7ff743aae
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156827B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes