N,N,N',N'-Tetramethylazodicarboxamide → {6-[5-(4-fluoro-3-trifluoromethyl-phenyl)-2-methyl-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 915462Notes

Reaction equation

HRID 915462 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[C:26]([CH2:30]O)[N:27]([CH3:29])[N:28]=2)=[CH:20][C:19]=1[C:32]([F:35])([F:34])[F:33].CN(C)C(N=NC(N(C)C)=O)=O.C(P(CCCC)CCCC)CCC>>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH2:30][C:26]3[N:27]([CH3:29])[N:28]=[C:24]([C:21]4[CH:22]=[CH:23][C:18]([F:17])=[C:19]([C:32]([F:34])([F:33])[F:35])[CH:20]=4)[CH:25]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl esterHCID 69280241[5-(4-fluoro-3-trifluoromethyl-phenyl)-2-methyl-2H-pyrazol-3-yl]-methanol

Product 1

HCID 69282809{6-[5-(4-fluoro-3-trifluoromethyl-phenyl)-2-methyl-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Procedure

In analogy to the procedure described for example 3 c], (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 2 e]) was reacted with [5-(4-fluoro-3-trifluoromethyl-phenyl)-2-methyl-2H-pyrazol-3-yl]-methanol in the presence of N,N,N′,N′-tetramethyl azodicarboxamide and tributylphosphine to give {6-[5-(4-fluoro-3-trifluoromethyl-phenyl)-2-methyl-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester as white solid.

Sources & evidence

ORD record
ord-0a8f1b37692a4a16b5f8d698a1f35f44
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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