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Sodium Carbonate → 4-(1-Phenyl-1-(3,5-difluorophenyl)-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 606739
Notes
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Reaction equation

HRID 606739 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[C:14](Br)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11](=[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:25]2[CH:24]=[C:23]([F:22])[CH:28]=[C:27]([F:29])[CH:26]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734338(3,5-Difluorophenyl)boronic acidHCID 590345854-(1-Bromo-1-phenyl-methylene)-piperidine-1-carboxylic Acid tert-butyl Ester

Product 1

HCID 670464874-(1-Phenyl-1-(3,5-difluorophenyl)-methylene)-piperidine-1-carboxylic Acid tert-butyl EsterYield 64%

Reagents, catalysts & solvents 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst
HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of 4-(1-bromo-1-phenyl-methylene)-piperidine-1-carboxylic acid tert-butyl ester (0.115 g, 0.33 mmol) and 3,5-difluorophenylboronic acid (0.052 g 0.33 mmol) in DME (3 mL) was added 2M sodium carbonate (0.65 mL, 1.30 mmol). The reaction vessel was then flushed with Ar for 10 minutes, Pd2 dba3 (0.015 g, 0.016 mmol) was added, the vessel was sealed and the mixture was heated at 90° C. for 16 h. The cooled mixture was filtered (0.45 μm syringe filter) and the filtrate was evaporated. The residue was purified by preparative HPLC to give the title compound (0.080 g, 64%) as a white solid:

Workup

  1. customThe reaction vessel was then flushed with Ar for 10 minutes
  2. customthe vessel was sealed
  3. filtrationThe cooled mixture was filtered
  4. filtration(0.45 μm syringe filter)
  5. customthe filtrate was evaporated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-e892db5ce8dd47a88ae4318e4100c652
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07915283B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes