HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 66793903, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Reactant | 5-Bromo-1,3-dihydro-1,3-dimethyl-2H-benzimidazol-2-one | HCID 47003447 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 66793903 | HCID 66793903 | 31.8% |
Reaction Steps
A mixture of 5-Bromo-1,3-dimethyl-1,3-dihydro-benzoimidazol-2-one (121 mg, 0.5 mmol), 3-pyridyl boronic acid (68 mg, 0.55 mmol), polymer-supported Pd(PPh3)4 (0.09 mmol/g, 278 mg, 0.025 mmol) and Na2CO3 (2 M in water, 0.55 mL, 1.1 mmol) in DME (3.3 mL) was heated to reflux for 1 hr. After filtration and concentration, the residue was purified by flash column (MeOH—CH2Cl2, v/v, 0-7.5%) and yielded the title compound (38 mg). MS (ESI) m/z 240.0 (M+H), retention time 1.00 min. 1H NMR (400 MHz, CD2Cl2) δ ppm 3.47 (s, 3H), 3.49 (s, 3H), 7.13 (d, J=8.1 Hz, 1H), 7.25 (s, 1H), 7.38-7.40 (m, 1H), 7.41-7.44 (m, 1H), 7.95-7.98 (m, 1H), 8.60 (m, 1H), 8.90 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08778972B2 |
| Source dataset | uspto-grants-2014_07 |
| ORD ID | ord-0820e4f295824495bb2dc66b6268e9e7 |
| Source note | uspto-grants-2014_07 |