2,6-Dichloropyridine → 4-[(4-Bromo-phenyl)-(6-chloro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726132Notes

Reaction equation

HRID 1726132 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](Cl)[N:27]=1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[O:15][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([Cl:25])[N:27]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 169892,6-DichloropyridineHCID 24758Sodium hydrideHCID 57603260Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylate

Product 1

HCID 866021274-[(4-Bromo-phenyl)-(6-chloro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(4-bromo-phenyl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.03 g, 2.78 mmol) in DMF (14 mL) was added NaH (60% in mineral oil, 278 mg, 6.95 mmol) and the mixture was stirred at room temperature for 10 minutes. 2,6-Dichloropyridine (1.23 g, 8.34 mmol) was added and the mixture was heated at 70° C. for 3 hours. Standard work-up and purification afforded 4-[(4-bromo-phenyl)-(6-chloro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester as an off white solid (1.28 g, 96%).

Workup

  1. temperaturethe mixture was heated at 70° C. for 3 hours
  2. customStandard work-up and purification

Sources & evidence

ORD record
ord-ca09888236074de998ea097d0903b4b9
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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