Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1) | HCID 17749886 | — |
| Reactant | HCID 58203926 | HCID 58203926 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58204047 | HCID 58204047 | 271.6% |
Reaction Steps
A suspension of 8-bromo-N-(2-chloro-5-(3,3-difluoroazetidine-1-carbonyl)phenyl)-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (400 mg, 0.70 mmol), Pd(OAc)2 (8 mg, 0.035 mmol), Xantphos (41 mg, 0.070 mmol), MeSO2(CH2)2NH2.HCl (169 mg, 1.06 mmol) and Na2CO3 (224 mg, 2.11 mmol) in toluene (5 mL) and DMF (5 mL) was heated at 80° C. under atmosphere of CO from balloon for 3 h. Then it was filtrated and concentrated, the crude product was purified by flash column chromatography on silica gel (petroleum ether: EtOAc=2:1-1:5 as eluted solvent) to give a white solid which was washed with DCM and dried to give 432 (121.3 mg, yield: 27%). 1H NMR (DMSO-d6, 400 MHz): δ 8.73-6.60 (m, 8H, NH, ArH), 4.75-3.02 (m, 18H). LC-MS: (ESI, m/z)=638 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08673952B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-131cd57a564744bc815f5f138237dd1c |
|---|
| Source note | uspto-grants-2014_03 |
|---|
