Triphenylphosphine → (3-Chloro-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-indol-1-yl)-acetic acid tert-butyl ester

HRID 1767920Notes

Reaction equation

HRID 1767920 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([Cl:18])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:20][C:21]1[N:22]=[C:23]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[S:24][C:25]=1[CH2:26][CH2:27]O.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:19])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH2:27][CH2:26][C:25]3[S:24][C:23]([C:29]4[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:36])[F:37])=[CH:33][CH:34]=4)=[N:22][C:21]=3[CH3:20])[CH:15]=2)[C:10]([Cl:18])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 226475832-[4-Methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]ethanolHCID 69283057tert-Butyl (3-chloro-6-hydroxy-1H-indol-1-yl)acetate

Product 1

HCID 69279677(3-Chloro-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-indol-1-yl)-acetic acid tert-butyl ester

Procedure

In analogy to the procedure described in example 3 c], (3-chloro-6-hydroxy-indol-1-yl)-acetic acid tert-butyl ester was reacted with 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethanol (example 5 c]) in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield (3-chloro-6-{2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-indol-1-yl)-acetic acid tert-butyl ester as light yellow oil.

Sources & evidence

ORD record
ord-9ea37af76f7744169ac7e6bab9fa9230
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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