HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Ethyl Bromide | HCID 6332 | — |
| Reactant | Caesium hydroxide--water (1/1/1) | HCID 23679066 | — |
| Reactant | HCID 178437952 | HCID 178437952 | — |
| Product | N-(3-ethyl-1-((1-ethyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide | HCID 67260505 | 24.2% |
Reaction Steps
To N-(1-((1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide (40 mg, 0.10 mmol; prepared as in Example 39, Step H) in dry DMF (519 μL, 0.10 mmol) was added bromoethane (11 mg, 0.10 mmol), cesium hydroxide hydrate (17 mg, 0.10 mmol) and 4 angstrom molecular sieves. The reaction mixture was stirred for one hour, filtered through an Acrodisk, rinsed with DCM and MeOH, and concentrated under a nitrogen stream to a residue. Preparative thin layer chromatography eluting with 10% MeOH, 0.5% NH4OH in CHCl3 provided the final product (10 mg). MS (ES+APCI) m/z=414 (M+H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08841455B2 |
| Source dataset | uspto-grants-2014_09 |
| ORD ID | ord-451488df66514331ae5b5baec9fced74 |
| Source note | uspto-grants-2014_09 |