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

HRID 915446

Reaction equation

HRID 915446 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([CH3:18])[CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][N:21]1[C:25]([CH2:26]O)=[CH:24][C:23]([C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)=[N:22]1.CN(C)C(N=NC(N(C)C)=O)=O.C(P(CCCC)CCCC)CCC>>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([CH3:18])[CH:13]=[C:14]([O:17][CH2:26][C:25]3[N:21]([CH3:20])[N:22]=[C:23]([C:28]4[CH:29]=[CH:30][C:31]([O:34][C:35]([F:37])([F:36])[F:38])=[CH:32][CH:33]=4)[CH:24]=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 44818672{1-methyl-3-[4-(trifluoromethoxy)phenyl]-1H-pyrazol-5-yl}methanolHCID 69280225(6-Hydroxy-4-methyl-indol-1-yl)-acetic acid tert-butyl ester

Product 1

HCID 69280239{4-methyl-6-[2-methyl-5-(4-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-indol-1-yl}-acetic acid tert-butyl ester

Procedure

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

Sources & evidence

ORD record
ord-9ace5926fa3a4610bff70c718a81d3d1
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Linked notes

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