HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → (7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl)(4-cyclopropyl-3-methoxyphenyl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | (4-Bromo-3-methoxy-phenyl)-(7'-chlorospiro[piperidine-4,4'-pyrrolo[2,1-c][1,4]benzoxazine]-1-yl)methanone | HCID 58551353 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | (7-Chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4'-piperidine]-1'-yl)(4-cyclopropyl-3-methoxyphenyl)methanone | HCID 58551518 | — |
Reaction Conditions
| Temperature | 120 °C |
|---|
Reaction Steps
To a microwave vial was added Pd-FibreCat (42 mg, 0.0065 mmol), (4-bromo-3-methoxyphenyl)(7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)methanone (63 mg, 0.13 mmol), cyclopropylboronic acid (17 mg, 0.19 mmol), DMF (0.7 mL), and K2CO3 (190 μL of 2.0 M, 0.39 mmol). The reaction vessel was purged with nitrogen and the mixture was heated at 120° C. overnight. The mixture was filtered and was purified by prep-HPLC (20-99% MeOH:H2O with HCl modifier) to give (7-chlorospiro[benzo[b]pyrrolo[1,2-d][1,4]oxazine-4,4′-piperidine]-1′-yl)(4-cyclopropyl-3-methoxyphenyl)methanone. ESI-MS m/z calc. 448.2, found 449.4 (M+1)+; Retention time: 3.32 minutes (4 min run).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09365588B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-330d2bf92cdb4e5b8bf89188f16bb743 |
| Source note | uspto-grants-2016_06 |