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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2215563Generated: October 31, 2026

Dimethylformamide → N1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide

https://huagongshe.com/reaction/2215563

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPhenyl MethylcarbamateHCID 16034—
ReactantSodium hydrideHCID 24758—
Reactant4-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamineHCID 21949282—
SolventWaterHCID 962—
ProductN1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamideHCID 2194921358.9%

Reaction Steps

Phenyl N-methylcarbamate (350 mg, Production example 2-1) was added to a solution of 4-(3-methyl-1H-5-indolyl)oxy-2-pyridinamine (500 mg), sodium hydride (93 mg) and N,N-dimethylformamide (5 ml) at room temperature; and the reaction mixture was stirred for 2 hours and 45 minutes. Water was added to the reaction mixture; extraction was performed with ethyl acetate; and purification was performed by NH-silica gel column chromatography (Fuji Silysia, hexane:ethyl acetate=1:2, sequentially, ethyl acetate) to yield the title compound as a pale yellow amorphous solid (365 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07109219B2
Source datasetuspto-grants-2006_09
ORD IDord-c366face41344ba383514b5435e315a3
Source noteuspto-grants-2006_09