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Pyridine → HCID 60110691, compound

HRID 1007483
Notes
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Reaction equation

HRID 1007483 reaction equation
[Si:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](B(O)O)=[CH:14][CH:15]=2)[C:10]([CH:20]([CH3:22])[CH3:21])=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:23][C:24]1[C:38]([CH3:39])=[CH:37][C:27]([O:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:26][C:25]=1[CH3:40].N1C=CC=CC=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:33]([O:32][C:30](=[O:31])[CH2:29][O:28][C:27]1[CH:26]=[C:25]([CH3:40])[C:24]([O:23][C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:9]=[C:10]3[CH:20]([CH3:22])[CH3:21])=[C:38]([CH3:39])[CH:37]=1)([CH3:36])([CH3:35])[CH3:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 22669367HCID 22669367, compoundHCID 22669607HCID 22669607, compound

Product 1

HCID 60110691HCID 60110691, compoundYield 63.4%

Reagents, catalysts & solvents 2

HCID 8895
Cupric acetate
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

0.50 g (1.58 mmol) of 1-[tert-butyl(dimethyl)silyl]-3-isopropyl-1H-indol-5-yl-boronic acid (Example XII), 0.437 g (173 mmol) of tert-butyl-(4-hydroxy-3,5-dimethylphenoxy)acetate (Example IX), 0.286 g (1.58 mmol) of copper(II) acetate and 0.50 g of molecular sieve (4 Å, powdered) are suspended in 10 ml of dried dichloromethane. 0.64 ml (7.88 mmol) of pyridine and 1.10 ml (7.88 mmol) of triethylamine are added dropwise at room temperature. The batch is stirred overnight at room temperature. The batch is subsequently filtered through silica gel and washed with dichloromethane. The filtrate is concentrated and the residue is filtered through silica gel (dichloromethane). 0.525 g (62%) of tert-butyl-[4-({1-[tert-butyl-(dimethyl)silyl]-3-isopropyl-1H-indol-5-yl}oxy)-3,5-dimethylphenoxy]acetate is obtained.

Workup

  1. filtrationThe batch is subsequently filtered through silica gel
  2. washwashed with dichloromethane
  3. concentrationThe filtrate is concentrated
  4. filtrationthe residue is filtered through silica gel (dichloromethane)

Sources & evidence

ORD record
ord-1c7cd122e58c4069af959ed965e110ca
Source dataset
uspto-grants-2004_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06794406B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes