P-Anisidine → HCID 11555320, compound

Participants

Role	Name	HCID	Charge
Reactant	P-Anisidine	HCID 7732	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
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	HCID 22025245	HCID 22025245	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 11555320	HCID 11555320	78%

Reaction Steps

To a suspension of 1-methyl-7-(pyridine-4-yloxy)-1H-indole-2-carboxylic acid (40 mg, 0.15 mmol) in DMF (1 mL) was added Hunig's base (52 microL, 0.3 mmol) resulting in a clear solution. After 5 min, HATU (90 mg, 0.23 mmol) and HOAT (3 mg, 0.02 mmol) were added followed by the above anisidine (39 mg, 0.15 mmol). The mixture was stirred overnight. The reaction mixture was diluted with EtOAc (30 mL), washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by column chromatography (eluting with 30-80% EtOAc in hexane) to give the title compound (60 mg, 78%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592332B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-a57ad4a8c0b54abcb6a8cdf634e36253
Source note	uspto-grants-2009_09