HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromopyridine 1-oxide → 2-(7-(4-(tert-Butoxycarbonylamino)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridine 1-oxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromopyridine 1-oxide | HCID 300057 | — |
| Reactant | tert-Butyl 3-fluoro-4-(2-iodothieno[3,2-b]pyridin-7-yloxy)phenylcarbamate | HCID 59457739 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 2-(7-(4-(tert-Butoxycarbonylamino)-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridine 1-oxide | HCID 68716807 | 57% |
Reaction Steps
A solution of 431 (460 mg, 0.94 mmol), 2-bromopyridine N-oxide (420 mg, 2.41 mmol), bistrimethyltin (294 μL, 465 mg, 1.42 mmol) and Pd(PPh3)4 (109 mg, 0.09 mmol) in dioxane (10 mL) was heated to reflux for 8 hrs under nitrogen. The reaction mixture was concentrated and purified by flash chromatography using the gradient 5-20% MeOH in EtOAc as an eluent yielding 432 (243 mg, 57% yield). LCMS: (M+H) 454.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07790729B2 |
| Source dataset | uspto-grants-2010_09 |
| ORD ID | ord-c4117b8a060b412f8c8c678f2c3361ee |
| Source note | uspto-grants-2010_09 |