N,N,N',N'-Tetramethylazodicarboxamide → 2-Methyl-2-(2-methyl-4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenoxy)-propionic acid ethyl ester

HRID 1242357Notes

Reaction equation

HRID 1242357 reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[CH:6][CH:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[N:3]=1.[CH2:21]([O:23][C:24](=[O:37])[C:25]([O:28][C:29]1[CH:34]=[CH:33][C:32](O)=[CH:31][C:30]=1[CH3:36])([CH3:27])[CH3:26])[CH3:22].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>C1COCC1>[CH2:21]([O:23][C:24](=[O:37])[C:25]([CH3:27])([O:28][C:29]1[CH:34]=[CH:33][C:32]([O:10][CH2:9][CH2:8][C:7]2[C:2]([CH3:1])=[N:3][C:4]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:20])[F:19])=[CH:13][CH:12]=3)=[CH:5][CH:6]=2)=[CH:31][C:30]=1[CH3:36])[CH3:26])[CH3:22]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 219358312-[2-Methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol

Product 1

HCID 670724952-Methyl-2-(2-methyl-4-{2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenoxy)-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.181 g (0.642 mmol) of the above prepared 2-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethanol and 0.153 g (0.642 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) were dissolved in 8 ml of abs. THF and treated successively at 0° C. with 0.156 g (0.771 mmol) of tributylphosphine and 0.133 g (0.770 mmol) of N,N,N′,N′-tetramethylazodicarboxamide. The cooling bath was then removed and stirring continued for one night. Filtration over a pad of Celite, evaporation of the solvent, followed by flash chromatography (SiO2, hexane/AcOEt=85/15), delivered 0.070 g of the title compound as colorless oil.

Workup

  1. dissolutionwere dissolved in 8 ml of abs
  2. customThe cooling bath was then removed
  3. waitcontinued for one night
  4. filtrationFiltration
  5. customover a pad of Celite, evaporation of the solvent

Sources & evidence

ORD record
ord-2d42e3703b4040aa916bae3ffbcec942
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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