Sodium hydride → 4-[(4-Bromo-phenyl)-(6-fluoro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726135Notes

Reaction equation

HRID 1726135 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+].[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](F)[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]([F:25])[N:27]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 739342,6-DifluoropyridineHCID 57603260Tert-butyl 4-((4-bromophenyl)(hydroxy)methyl)piperidine-1-carboxylate

Product 1

HCID 689728724-[(4-Bromo-phenyl)-(6-fluoro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(4-bromo-phenyl)-hydroxy-methyl]-piperidine-1-carboxylic acid tert-butyl ester (1.36 g, 3.67 mmol) in DMF (18 mL) was added NaH (60% in mineral oil, 367 mg, 9.17 mmol) and the mixture was stirred at room temperature for 10 minutes. 2,6-Difluoropyridine (1.00 mL, 11.0 mmol) was added and the mixture was heated at 70° C. overnight. Work-up and purification gave 4-[(4-bromo-phenyl)-(6-fluoro-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester as an off-white solid (1.60 g, 94%).

Workup

  1. temperaturethe mixture was heated at 70° C. overnight
  2. custompurification

Sources & evidence

ORD record
ord-92f496bb81ca4d4aa16190d1aa66630a
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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