Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-(Methanesulfonyl)phenylboronic acid | HCID 2734364 | — |
| Reactant | tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate | HCID 136331866 | — |
| Catalyst | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 69087719 | HCID 69087719 | — |
Reaction Steps
A mixture of tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (50 mg, 0.097 mmol), [4-(methyl sulfonyl)phenyl]boronic acid (39 mg, 0.20 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (7 mg, 0.1 mmol), and 2M Na2CO3 aq. (0.097 mL, 0.20 mmol) in DMF (1.5 mL) was treated with microwave (160° C. for 1 hour). The mixture was diluted with AcOEt, washed with water (×3), brine, dried over Na2SO4, and then filtrated through Celite pad. The filtrate was concentrated and the residue was purified by preparative thin-layer chromatography (n-hexane/AcOEt=1:1×2) to afford the mixture of the desired product and tert-butyl {1-[4-(2-chloro-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl)cyclobutyl}carbamate (51 mg) as a yellow solid. LCMS: 634 [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08569331B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-34ce6d41aa1f414ea1719d3eb898c10e |
|---|
| Source note | uspto-grants-2013_10 |
|---|