Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Bromo-2-fluoroaniline | HCID 123050 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | HCID 58380548 | HCID 58380548 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67194489 | HCID 67194489 | 48% |
Reaction Steps
Palladium acetate (129 mg, 0.001 mol), BINAP (538 mg, 0.001 mol), cesium carbonate (2.8 g, 0.009 mol) were dissolved in toluene (20 mL) and the resulting mixture was sparged for 30 mins with nitrogen. This was followed by addition of trifluoro-methanesulfonic acid 1-benzyl-6-methyl-8-nitro-5-oxo-1,2,3,5-tetrahydro-imidazo[1,2-a]pyridin-7-yl ester (2.5 g, 0.006 mol) and 4-bromo-2-fluoro-phenylamine (1.15 g, 0.006 mol) in toluene (20 mL) and the reaction flask was again sparged for another 15 minutes. The reaction mixture was heated at 90° C. for 1 hour. The reaction was monitored by TLC (80% ethylacetate in hexane). The reaction mixture was filtered through celite bed and concentrated. Purification by column chromatography on silica gel (40% ethylacetate in hexane) afforded 1.3 g of the product (48% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08466289B2 |
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| Source dataset | uspto-grants-2013_06 |
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| ORD ID | ord-dffd0f3ac9264a568942bd134deb4178 |
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| Source note | uspto-grants-2013_06 |
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