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 | Methylamine hydrochloride | HCID 6364545 | — |
| Reactant | HCID 58203926 | HCID 58203926 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58203693 | HCID 58203693 | 317.6% |
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), MeNH2.HCl (71 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 4 h, and then filtered and concentrated. The crude product was purified by pre-HPLC to give 448 (121.4 mg, yield 32%). 1H NMR (DMSO, 400 MHz): δ 8.45 (m, 1H, NH), 7.98-7.44 (m, 6H, ArH), 6.60 (s, 1H, ═CH), 4.75 (brs, 2H, CH2), 4.48 (br s, 2H, CH2), 4.20 (s, 2H, CH2), 3.30 (s, 3H, CH3), 2.99 (s, 2H, CH2), 2.75 (d, J=4.4 Hz, 3H, CH3). LC-MS: (ESI, m/z)=546 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08263633B2 |
|---|
| Source dataset | uspto-grants-2012_09 |
|---|
| ORD ID | ord-0e9525399a8b4255b529215f75f1ccc8 |
|---|
| Source note | uspto-grants-2012_09 |
|---|
