HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Phosphate, Tribasic → 1-Benzyl-7-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 58380548 | HCID 58380548 | — |
| Reactant | 2-Fluoro-4-(trimethylsilyl)aniline | HCID 59596599 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 1-Benzyl-7-(2-fluoro-4-trimethylsilanyl-phenylamino)-6-methyl-8-nitro-2,3-dihydro-1H-imidazo[1,2-a]pyridin-5-one | HCID 67193684 | 85.7% |
Reaction Steps
Trifluoro-methanesulfonic acid 1-benzyl-6-methyl-8-nitro-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-7-yl ester (I-1e: 500 mg, 0.001 mol) in toluene (15 mL) was reacted with 2-fluoro-4-trimethylsilanyl-phenylamine (221 mg, 0.001 mol) in the presence of Pd2(dba)3 (63.3 mg, 0.0001 mol), xantphos (40 mg, 0.0001 mol) and K3PO4 (367 mg, 0.002 mol) and the reaction mixture was heated to reflux for 1 hour. Reaction workup yields the crude product which was purified by column chromatography on silica gel (40% ethylacetate in hexane) to afford 400 mg of the product (74.48% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08466289B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-8ebe49e6572f4199a17b165266a5e29a |
| Source note | uspto-grants-2013_06 |