Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Carboxyphenylboronic acid | HCID 2733957 | — |
| Reactant | HCID 58149871 | HCID 58149871 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 44476773 | HCID 44476773 | 10.2% |
Reaction Steps
Sodium carbonate (85 mg) and PdCl2(dppf)2 (50 mg) were added sequentially to a suspension of 1-bromo-5-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)isoquinoline (D40; 180 mg) and 3-(dihydroxyboranyl)benzoic acid (Aldrich; 99 mg) in 1,2-dimethoxyethane (DME; 2 ml), ethanol (1 ml) and water (1 ml). The resulting suspension was heated to 80° C. and stirred for overnight. The solvent was evaporated in vacuo and the residue was purified by MDAP to give the title compound (20 mg). δH (DMSO-d6, 400 MHz): 1.37 (6H, d), 4.90 (1H, m), 7.48 (1H, d), 7.73 (1H, t), 7.86 (1H, t), 7.95 (1H, dd), 8.19 (5H, m), 8.60 (1H, dd), 8.78 (2H, m), 13.17 (1H, br s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08329730B2 |
|---|
| Source dataset | uspto-grants-2012_12 |
|---|
| ORD ID | ord-b0db569870d446d09fba6ae8d00c2206 |
|---|
| Source note | uspto-grants-2012_12 |
|---|
