2-Thiophenecarboxylic acid → HCID 57901607, compound

Participants

Role	Name	HCID	Charge
Reactant	2-Thiophenecarboxylic acid	HCID 10700	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	1H-Indole-2-carboxylic acid, 7-amino-, ethyl ester	HCID 11138194	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	HCID 57901607	HCID 57901607	83%

Reaction Conditions

Temperature	60 °C

Reaction Steps

A mixture of ethyl 7-amino-1H-indole-2-carboxylate (0.40 g), thiophene-2-carboxylic acid (0.28 g), ethyldiisopropylamine (0.75 mL), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.82 g) and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 18 hr. The reaction mixture was diluted with ethyl acetate, washed with aqueous citric acid solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:97-3:7) to give the title compound (510 mg, yield 83%) as a pale-yellow amorphous solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08957070B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-54e6bd638db54838ae583cd7335f4987
Source note	uspto-grants-2015_02