HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Phenyl Methylcarbamate | HCID 16034 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 4-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamine | HCID 21949282 | — |
| Solvent | Water | HCID 962 | — |
| Product | N1,3-Dimethyl-5-(2-amino-4-pyridyl)oxy-1H-1-indolecarboxamide | HCID 21949213 | 58.9% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07109219B2 |
| Source dataset | uspto-grants-2006_09 |
| ORD ID | ord-c366face41344ba383514b5435e315a3 |
| Source note | uspto-grants-2006_09 |