1H-Indole-7-carboxylic acid → [Rac]-1h-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amide

Participants

Role	Name	HCID	Charge
Reactant	1H-Indole-7-carboxylic acid	HCID 74281	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate	HCID 2733207	—
Reactant	2-{[(4-tert-Butylphenyl)methyl]amino}-1-(3,4-dichlorophenyl)ethan-1-ol	HCID 69342357	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	[Rac]-1h-indole-7-carboxylic acid (4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amide	HCID 69513518	62.4%

Reaction Steps

To a solution of 36 mg (0.22 mmol) of 1H-indole-7-carboxylic acid and 72 mg of TBTU (0.22 mmol) in 3 ml DMF, were added 0.19 ml (1.12 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 79 mg (0.22 mmol) of [rac]-(4-tert-butyl-benzyl)-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethyl]-amine was added. After stirring for 17 h at rt, the reaction mixture was diluted with 30 ml water and extracted with EtOAc (2×). The combined organic phases were washed with water and brine, dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography (8 g silica gel; heptane/EtOAc 2:1) to give 68 mg (59%) of an off-white solid. MS (ISP) 495.4 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07259183B2
Source dataset	uspto-grants-2007_08
ORD ID	ord-4964d2ea9c244e0188c16faced25084a
Source note	uspto-grants-2007_08