HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole → 3-Butyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole | HCID 23102914 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 3-Butyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole | HCID 68638577 | — |
Reaction Steps
0.39 ml of n-butyllithium solution (1.6M in hexane) is added at −75° C. to a 0.5 M solution of zinc chloride in THF and the resulting mixture stirred for 30 min at room temperature. This solution is added via a syringe to a solution of 107 mg 3-iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole (9b) and 10 mg 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride (1:1 complex with CH2Cl2) in THF and stirred for 4 h at 70° C. The reaction mixture is quenched by adding saturated NH4Cl-solution and extracted with ethylacete. The combined organic layers are dried over MgSO4, the solvens removed in vacuo. Reversed phase chromatography (RP18, water (0.05% HCOOH)/acetonitrile (0.05% HCOOH)) 30 mg product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07709466B2 |
| Source dataset | uspto-grants-2010_05 |
| ORD ID | ord-ce0752f0270045b5b9b1a220592a7eee |
| Source note | uspto-grants-2010_05 |