HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 11660010, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | 2-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole | HCID 11681546 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 11660010 | HCID 11660010 | 82.6% |
Reaction Steps
2-(4-Bromo-phenyl)-5-methyl-4-(2-pyrrolidin-1-yl-ethyl)-oxazole (See Example 8) (7.23 g, 21.57 mmol), 4-pyridylboronic acid (3.98 g, 32.35 mmol), [1,1 bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with CH2Cl2 (1:1) (0.616 g, 0.755 mmol), and aqueous sodium carbonate (2M, 40 mL) are dissolved in 200 mL of dioxane and heated to reflux for 1.5 hours. The mixture is concentrated to a dark residue and purified by flash silica gel chromatography (gradient: 3-6% 2M NH3 in MeOH/dichloromethane) to provide the titled compound (5.94 g, 82.5% yield). MS (m/e): 334.2 (M+1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07666871B2 |
| Source dataset | uspto-grants-2010_02 |
| ORD ID | ord-e40ae1c43f664e8fbbcf2c307781e998 |
| Source note | uspto-grants-2010_02 |