HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(6-Chloropyridin-2-yl)-1-methyl-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1,4-Dioxane | HCID 31275 | — |
| Reactant | 2-Chloro-6-iodopyridine | HCID 18931860 | — |
| Reactant | (1-Methyl-1H-indol-2-yl)boronic acid | HCID 22733820 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-(6-Chloropyridin-2-yl)-1-methyl-1H-indole | HCID 86700704 | 100.2% |
Reaction Steps
2-Chloro-6-iodopyridine (400 mg, 1.67 mmol), N-methylindole-2-boronic acid (292 mg, 1.67 mmol), tetrakis(triphenylphosphine)palladium (0) (154 mg, 0.13 mmol) and Na2CO3 (442 mg, 4.18 mmol) were dissolved in water (10 mL) and dioxane (10 mL) and heated using a microwave (110° C., absorption high) for 1 h. The solvents were removed in vacuo and the residue was partitioned between DCM (50 mL) and water (30 mL). The aq fraction was extracted with DCM (30 mL) and the combined organic fractions were dried (MgSO4) and concentrated in vacuo to give the crude title compound (406 mg) as a brown gum. LCMS (ES+): 243.2 [MH]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09353086B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-548650d19e1f4a4f8b1a473ecfd73a68 |
| Source note | uspto-grants-2016_05 |