Diisopropylethylamine → 2-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Bromo-4-methylbenzoic acid	HCID 226292	—
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	Ethyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate	HCID 10921653	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(2-Bromo-4-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester	HCID 59314151	76%

Reaction Steps

To a solution of 2-bromo-4-methyl-benzoic acid (314 mg, 1.46 mmol), 2-amino-indan-2-carboxylic acid ethyl ester (300 mg, 1.46 mmol), HATU (666 mg, 1.75 mmol) in anhydrous DMF (1.8 mL) is added DIPEA (381 μL, 2.19 mmol). The resulting solution is stirred at RT overnight. Poured reaction into water (10 mL) and extracted with EtOAc (3×5 mL). The combined organic layers and concentrated in vacuo. The residue is purified by flash column chromatography (12 g silica gel, gradient elution: 0-30% EtOAc in heptane) to give product (276) as off-white solid (445 mg, 76%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08569535B2
Source dataset	uspto-grants-2013_10
ORD ID	ord-91d45f760fed431cb70cd3500df63914
Source note	uspto-grants-2013_10