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

HRID 1242527Notes

Reaction equation

HRID 1242527 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].[CH:18]1([CH2:21][C:22]2[C:27]([CH2:28]O)=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=[C:24]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:41]([F:44])([F:43])[F:42])=[CH:36][CH:35]=3)[N:23]=2)[CH2:20][CH2:19]1.CN(C)C(N=NC(N(C)C)=O)=O.C(P(CCCC)CCCC)CCC>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:28][C:27]2[C:22]([CH2:21][CH:18]3[CH2:20][CH2:19]3)=[N:23][C:24]([C:34]3[CH:35]=[CH:36][C:37]([O:40][C:41]([F:44])([F:42])[F:43])=[CH:38][CH:39]=3)=[CH:25][C:26]=2[C:30]([F:31])([F:33])[F:32])=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoateHCID 21935688[2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-yl]-methanol

Product 1

HCID 865978232-{4-[2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester

Procedure

In analogy to the procedure described in example 43E], 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) was reacted with [2-cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-yl]-methanol in the presence of N,N,N′,N′-tetramethylazodicarboxamide and tributylphosphine to give the title compound as colorless crystals.

Sources & evidence

ORD record
ord-56f3824fcb024547bb7297ddf5368ebc
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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