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

HRID 915484Notes

Reaction equation

HRID 915484 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][CH:18]([F:37])[N:19]1[C:23]([CH2:24]O)=[CH:22][C:21]([C:26]2[CH:31]=[CH:30][C:29]([O:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=2)=[N:20]1.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][CH2:24][C:23]3[N:19]([CH:18]([F:37])[F:17])[N:20]=[C:21]([C:26]4[CH:27]=[CH:28][C:29]([O:32][C:33]([F:35])([F:34])[F:36])=[CH:30][CH:31]=4)[CH:22]=3)[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 67402865[2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanolHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 69282437{6-[2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-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 [2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanol in the presence of N,N,N′,N′-tetramethyl azodicarboxamide and tributylphosphine to give {6-[2-difluoromethyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester as white solid.

Sources & evidence

ORD record
ord-2c43f4574a0c4c2fb7701e84f33c3295
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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