HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Ethyl 3-(6-cyanopyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | 5-Bromopyridine-2-carbonitrile | HCID 817154 | — |
| Reactant | Ethyl 8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate | HCID 117728723 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | Ethyl 3-(6-cyanopyridin-3-yl)-8-morpholinoimidazo[1,2-b]pyridazine-2-carboxylate | HCID 117728523 | — |
Reaction Steps
Using the procedure described in Example 20, Step A, the title compound was prepared from Compound 5c (1.38 g, 5.00 mmol), 5-bromo-2-cyanopyridine (1.42 g, 7.50 mmol), Pd(OAc)2 (78.6 mg, 0.350 mmol), PPh3 (91.8 mg, 0.350 mmol), and KOAc (1.47 g, 15.0 mmol) in DMA (20 mL) at 110° C. for 16 h. 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.00 (s, 1H), 8.20 (dd, J=8.1, 1.7 Hz, 1H), 8.05 (d, J=5.6 Hz, 1H), 7.83 (d, J=8.1 Hz, 1H), 6.17 (d, J=5.6 Hz, 1H), 4.36 (q, J=7.3 Hz, 2H), 4.02-4.13 (m, 4H), 3.90-3.99 (m, 4H), 1.30 (t, J=7.1 Hz, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C19H18N6O3: 379.2 (M+H). Found: 379.1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09193736B2 |
| Source dataset | uspto-grants-2015_11 |
| ORD ID | ord-de9e00b271d6419f953d0080a87a8683 |
| Source note | uspto-grants-2015_11 |