HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 7-Chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2,6-Dichloro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine | HCID 44516386 | — |
| Reactant | 3-Bromo-7-chloroimidazo[1,2-a]pyridine | HCID 46739118 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 7-Chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine | HCID 86644346 | — |
Reaction Steps
3-Bromo-7-chloro-imidazo[1,2-a]pyridine (1 eq, 3.02 mmol, 700 mg) and 2,6-dichloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (1.1 eq, 3.32 mmol, 1.01 g) are dissolved in DME (4 ml) and water (1 ml) and Na2CO3 (1.5 eq, 5.53 mmol, 562 mg) is added. PdCl2(PPh3)2 (0.1 eq, 0.3 mmol, 212 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 15 min. At the completion of this time the solvent is removed in vacuo and the reaction mixture is purified by flash column chromatography eluting with 9:1 DCM/MeOH to yield 7-chloro-3-(2,6-dichloro-pyridin-4-yl)-imidazo[1,2-a]pyridine as a yellow solid; [M+H]+=299
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08367662B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-6000b44755944df5bd3517ca750018c6 |
| Source note | uspto-grants-2013_02 |