Triphenylphosphine → (6-{2-[2-(4-Trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy]-indol-1-yl)-acetic acid tert-butyl ester

HRID 1767915Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[F:19][C:20]([F:36])([F:35])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33]O)[N:31]=2)=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>>[C:1]([O:5][C:6](=[O:18])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:33][CH2:32][C:30]3[N:31]=[C:27]([C:24]4[CH:23]=[CH:22][C:21]([C:20]([F:36])([F:19])[F:35])=[CH:26][CH:25]=4)[S:28][CH:29]=3)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 97268Di-tert-butyl azodicarboxylate

HCID 106122852-[2-(4-Trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol

HCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69280485(6-{2-[2-(4-Trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy]-indol-1-yl)-acetic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 3 c], (6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester (example 6 b]) was reacted with 2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield (6-{2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy]-indol-1-yl)-acetic acid tert-butyl ester as yellow oil.

Sources & evidence

ORD record: ord-7547652b432946908c117c5cb9aa751c
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235572B2

Reaction notes

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