Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Chloroiodomethane | HCID 11644 | — |
| Reactant | HCID 178517591 | HCID 178517591 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71295679 | HCID 71295679 | 16% |
Reaction Steps
To a solution of 5-bromo-3-(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-2-yl)pyridin-2-ol (0.3 g, 1.02 mmol) and Cesium carbonate (0.663 g, 2.04 mmol) in DMF (10 mL), was heated to 100° C. Then chloroiodomethane (215 mg, 1.22 mmol) was added by dropwise, the react mixture was stirred at 100° C. for 30 minutes. The solvent was removed off and the resulting residue was purified using flash column (petroleum ether:EtOAc 3:1) to provide 2-bromo-8,9,10,11-tetrahydro-6H-benzo[4,5]imidazo[1,2-c]pyrido[3,2-e][1,3]oxazine (50 mg, yield 16%) as a solid. 1HNMR (400 MHz, CDCl3): δ=8.30 (d, J=2.4 Hz, 1H), 8.20 (d, J=2.4 Hz, 1H), 5.87 (s, 2H), 2.66˜2.68 (m, 2H), 2.58˜2.61 (m, 2H), 1.87˜1.88 (m, 4H). MS (M+H)+: 306/308.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09265773B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-9c9064d302844b08bf2457d6e9eebb51 |
|---|
| Source note | uspto-grants-2016_02 |
|---|