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 67050629 | HCID 67050629 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 67050608 | HCID 67050608 | 183.6% |
Reaction Steps
A suspension of 2-(3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzamido)ethyl acetate (400 mg, 0.69 mmol), Pd(OAc)2 (10 mg, 0.045 mmol), Xantphos (40 mg, 0.069 mmol), MeSO2CH2CH2NH2.HCl (165 mg, 1.04 mmol) and Na2CO3 (219 mg, 2.07 mmol) in toluene (5 mL) was heated at 80° C. under atmosphere of CO from balloon overnight. Then it was filtrated and concentrated, the crude product was purified by column (EtOAc: MeOH=10:1) to afford 385 (76.8 mg, yield: 18%). 1HNMR (DMSO-d6, 400 MHz): δ8.70 (t, J=5.6 Hz, 1H), 8.61 (d, J=5.6 Hz, 1H), 8.07-7.41 (m, 6H), 6.57 (s, 1H), 4.72 (s, 1H), 4.71 (t, J=5.6 Hz, 1H), 3.63-2.95 (m, 16H). LC-MS: (ESI, m/z)=606 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08673952B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-a18b6adad46b40efb541622c43568270 |
|---|
| Source note | uspto-grants-2014_03 |
|---|
