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

HRID 1242373Notes

Reaction equation

HRID 1242373 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[C:10]([CH2:11][OH:12])=[CH:9][CH:8]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[N:6]=1)[CH3:3].[CH2:23]([O:25][C:26](=[O:39])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34](O)=[CH:33][C:32]=1[CH3:38])([CH3:29])[CH3:28])[CH3:24].C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>C1COCC1>[CH2:23]([O:25][C:26](=[O:39])[C:27]([O:30][C:31]1[CH:36]=[CH:35][C:34]([O:12][CH2:11][C:10]2[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])=[N:6][C:7]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)=[CH:8][CH:9]=2)=[CH:33][C:32]=1[CH3:38])([CH3:28])[CH3:29])[CH3:24]

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935887HCID 21935887, compound

Product 1

HCID 670722672-{4-[2-Dimethylaminomethyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.170 g (0.548 mmol) of the above prepared [2-dimethylaminomethyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-methanol and 0.122 g (0.512 mmol) of 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) were dissolved in 6 ml of abs. THF and treated successively at 0° C. with 0.133 g (0.658 mmol) of tributylphosphine and 0.114 g (0.659 mmol) of N,N,N′,N′-tetramethylazodicarboxamide. The cooling bath was then removed and stirring continued for additional 6 h. The reaction mixture was then poured onto crashed ice, extracted twice with AcOEt, washed with water and brine, and dried over magnesium sulfate. Evaporation of the solvents i. V., followed by flash chromatography (SiO2, hexane/AcOEt=25/75) yielded 0.016 g of the title product as yellow oil.

Workup

  1. dissolutionwere dissolved in 6 ml of abs
  2. customThe cooling bath was then removed
  3. additionThe reaction mixture was then poured
  4. extractionextracted twice with AcOEt
  5. washwashed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvents i

Sources & evidence

ORD record
ord-a0481be985f54ba8bddd0f771621380c
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

Loading…