2-Bromopyridine → {3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-pyridin-2-yl-phenoxy]-phenyl}-acetic acid ethyl ester

HRID 885282Notes

Reaction equation

HRID 885282 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16](B3OC(C)(C)C(C)(C)O3)=[CH:15][C:14]=2[CH2:28][N:29]2[C@@H:33]([CH3:34])[C@@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:41])[CH:7]=1)[CH3:2].Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH2:1]([O:3][C:4](=[O:42])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)=[CH:15][C:14]=2[CH2:28][N:29]2[C@@H:33]([CH3:34])[C@@H:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[O:31][C:30]2=[O:41])[CH:7]=1)[CH3:2]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 58237457{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-phenyl}-acetic acid ethyl ester

Product 1

HCID 58237583{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-pyridin-2-yl-phenoxy]-phenyl}-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

{3-[2-((4S,5R)-4-Methyl-2-oxo-5-phenyl-oxazolidin-3-ylmethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-phenyl}-acetic acid ethyl ester (0.1 g, 0.18 mmol), 2-bromopyridine (0.042 g, 0.26 mmol), potassium carbonate (0.061 g, 0.44 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.020 g, 0.02 mmol) were combined in 2:1 DME:H2O (4 mL) and degassed with N2 for 10 minutes. The reaction was then heated to 90° C. for 3.5 hours. The mixture was neutralized to pH 6 with 10% aqueous HCl and extracted with EtOAc. The crude material was purified by silica gel chromatography to give the desired product.

Workup

  1. customH2O (4 mL) and degassed with N2 for 10 minutes
  2. extractionextracted with EtOAc
  3. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-088dcee9803b4c8982d3112f5c47e067
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

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