N,N,N',N'-Tetramethylazodicarboxamide → [Rac]-(6-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-indol-1-yl)-acetic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	N,N,N',N'-Tetramethylazodicarboxamide	HCID 4278	—
Reactant	Tributylphosphine	HCID 13831	—
Reactant	[Rac]-2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl)-propan-1-ol	HCID 22647459	—
Reactant	tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate	HCID 69283069	—
Product	[Rac]-(6-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-indol-1-yl)-acetic acid tert-butyl ester	HCID 69279721	—

Reaction Steps

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 [rac]-2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-1-ol [PCT Int. Appl. (2002), WO 02/062774 A1] in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield [rac]-(6-{2-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propoxy}-indol-1-yl)-acetic acid tert-butyl ester as light yellow gum.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07235572B2
Source dataset	uspto-grants-2007_06
ORD ID	ord-da1223c8b53042bfac33a7d4c2590af3
Source note	uspto-grants-2007_06