HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 6-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Cyclopropanesulfonyl chloride | HCID 2760919 | — |
| Reactant | 6-(4-Bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one | HCID 67236633 | — |
| Product | 6-(4-Bromo-2-fluoro-phenyl)-8-cyclopropanesulfonyl-4,5-difluoro-6,8-dihydro-imidazo[4',5':3,4]benzo[1,2-d]oxazol-7-one | HCID 67236584 | 48.5% |
Reaction Steps
Intermediate I-25a was prepared from 6-(4-bromo-2-fluoro-phenyl)-4,5-difluoro-6,8-dihydro-imidazo[4′,5′:3,4]benzo[1,2-d]oxazol-7-one (I-16a: 220 mg, 0.57 mmol), cyclopropanesulfonyl chloride (120 mg, 0.86 mmol) and NaH (34 mg, 0.86 mmol) using procedures analogous to those described above for Intermediate I-19a to afford 135 mg of the product (48.5% yield). H1NMR (DMSO-d6, 300 MHz): δ 8.97 (s, 1H), 7.97 (dd, 1H), 7.80 (t, 1H), 7.70 (dd, 1H), 3.54-3.44 (m, 1H), 1.48-1.39 (m, 2H), 1.34-1.26 (m, 2H). HPLC: 94.1%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08614239B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-00ab844180ce4cf8befa997c2dd9915e |
| Source note | uspto-grants-2013_12 |