HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (3-(1H-pyrazol-1-yl)phenyl)boronic acid | HCID 16640530 | — |
| Reactant | 3-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide | HCID 68484431 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide | HCID 25262355 | — |
Reaction Steps
3-(3-Bromo-imidazo[1,2-a]pyridine-7-yl)-N-methyl-benzamide (Intermediate EA) (1 eq, 0.303 mmol, 100 mg) and 3-(1H-pyrazolyl)-phenylboronic acid (1.3 eq, 0.394 mmol, 74 mg) are dissolved in DME (3 ml) and water (0.8 ml) and Na2CO3 (3 eq, 0.909 mmol, 96.3 mg) is added. PdCl2(PPh3)2 (0.05 eq, 0.015 mmol, 10.6 mg) is added and the reaction mixture is heated using microwave radiation at 120° C. for 10 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 N-methyl-3-[3-(3-pyrazol-1-yl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-benzamide as a light brown solid; [M+H]+=395
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08367662B2 |
| Source dataset | uspto-grants-2013_02 |
| ORD ID | ord-b4ef440985944f6ca8d66ed403e850e8 |
| Source note | uspto-grants-2013_02 |