N,N,N',N'-Tetramethylazodicarboxamide → {6-[5-(3-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester

HRID 751183Notes

Reaction equation

HRID 751183 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]([F:33])([F:32])[O:19][C:20]1[CH:21]=[C:22]([C:26]#[C:27][CH2:28][CH2:29][CH2:30]O)[CH:23]=[CH:24][CH:25]=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][CH2:30][CH2:29][CH2:28][C:27]#[C:26][C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][C:18]([F:17])([F:32])[F:33])[CH:21]=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 688216934-Pentyn-1-ol, 5-[3-(trifluoromethoxy)phenyl]-

Product 1

HCID 68822183{6-[5-(3-Trifluoromethoxy-phenyl)-pent-4-ynyloxy]-indol-1-yl}-acetic acid ethyl ester

Procedure

In analogy to the procedure described for example 1 d], (6-hydroxy-indol-1-yl)-acetic acid ethyl ester (example 1 c]) was reacted with 5-(3-trifluoromethoxy-phenyl)-pent-4-yn-1-ol in the presence of N,N,N′,N′-tetramethyl azodicarboxamide and tributylphosphine to give the title compound as colorless oil.

Workup

  1. customdescribed for example 1 d

Sources & evidence

ORD record
ord-4745d46f663d462094938be8d48c0311
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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