Triphenylphosphine → 3-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid ethyl ester

HRID 215831Notes

Reaction equation

HRID 215831 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:13]=[N:14][C:15]([OH:18])=[CH:16][CH:17]=2)[CH:6]=1)[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:22]=1[C:28]1[C:32]([CH2:33]O)=[C:31]([CH:35]([CH3:37])[CH3:36])[O:30][N:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:13]=[N:14][C:15]([O:18][CH2:33][C:32]3[C:28]([C:22]4[C:21]([Cl:20])=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:27])=[N:29][O:30][C:31]=3[CH:35]([CH3:37])[CH3:36])=[CH:16][CH:17]=2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanolHCID 178468932HCID 178468932, compound

Product 1

HCID 672972823-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid ethyl esterYield 41.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a suspension of 3-(6-hydroxy-pyridin-3-yloxy)-benzoic acid ethyl ester (0.20 g, 0.77 mmol), [3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-yl]-methanol (0.22 g, 0.77 mmol), triphenylphosphine (0.242 g, 0.92 mmol) in benzene (10 ml) was added dropwise diisopropyldiazenedicarboxylate (0.202 g, 1.00 mmol). The reaction mixture was stirred at room temperature for 4 h and concentrated under reduced pressure. The resulting residue was further purified by column chromatography using silica (eluent hexanes-ethyl acetate 5:1) to give 0.167 g (41%) of 3-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid ethyl ester as colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was further purified by column chromatography

Sources & evidence

ORD record
ord-c89b82e12daa43e5a7663ad614ef8b9e
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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