1H-Indole-7-carboxylic acid → HCID 86603101, compound

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	N-[[4-(1,1-Dimethylethyl)phenyl]methyl]-3-methoxybenzeneethanamine	HCID 39418093	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 86603101	HCID 86603101	76.3%

Reaction Steps

To a solution of 80 mg of 1H-indole-7-carboxylic acid (0.5 mmol) and 159 mg of TBTU (0.5 mmol) in 10 ml DMF, were added 0.425 ml (2.48 mmol) of N,N-diisopropylethyl amine. After stirring for 5 min at rt, 174 mg (0.68 mmol) of (4-tert-butyl-benzyl)-[2-(3-methoxy-phenyl)-ethyl]-amine were added. After stirring for 3 h at rt, the reaction mixture was diluted with 50 ml water and extracted twice with EtOAc. 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 (40 g silica gel; heptane/EtOAc 2:1) to give 168 mg (75%) of a white solid. MS (ISP) 441.4 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07259183B2
Source dataset	uspto-grants-2007_08
ORD ID	ord-cd377f00830a41e5aa8f9d84f2169737
Source note	uspto-grants-2007_08