N,N,N',N'-Tetramethylazodicarboxamide → {6-[2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

HRID 890490Notes

Reaction equation

HRID 890490 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].[CH:17]1([CH2:20][C:21]2[C:26]([CH2:27]O)=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=[C:23]([C:33]3[CH:38]=[CH:37][C:36]([O:39][C:40]([F:43])([F:42])[F:41])=[CH:35][CH:34]=3)[N:22]=2)[CH2:19][CH2:18]1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>>[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][CH2:27][C:26]3[C:21]([CH2:20][CH:17]4[CH2:19][CH2:18]4)=[N:22][C:23]([C:33]4[CH:34]=[CH:35][C:36]([O:39][C:40]([F:43])([F:41])[F:42])=[CH:37][CH:38]=4)=[CH:24][C:25]=3[C:29]([F:30])([F:32])[F:31])[CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 21935688[2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-yl]-methanolHCID 68821422(6-Hydroxy-indol-1-yl)-acetic acid ethyl ester

Product 1

HCID 86597786{6-[2-Cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Procedure

In analogy to the procedure described in example 5 f], (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 6 b]) was reacted with [2-cyclopropylmethyl-6-(4-trifluoromethoxy-phenyl)-4-trifluoromethyl-pyridin-3-yl]-methanol in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield the title compound as colorless solid.

Sources & evidence

ORD record
ord-ae6422a02fae41f297ddfe0302d26be4
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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