HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1919078Generated: November 3, 2026
1,2-Dimethoxyethane → HCID 86661257, compound
https://huagongshe.com/reaction/1919078
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Bromo-1-methyl-3-(5-(1-methylazetidin-3-yl)pyridin-2-ylamino)pyridine-2(1H)-one | HCID 58044083 | — |
| Reactant | 2-(7,7-dimethyl-1-oxo-3,4,7,8-tetrahydro-1H-cyclopenta[4,5]pyrrolo[1,2-a]pyrazin-2(6H)-yl)-4-fluoro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate | HCID 67016232 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86661257 | HCID 86661257 | 31.3% |
Reaction Steps
A microwave tube equipped with a magnetic stirrer was charged with 5-bromo-1-methyl-3-(5-(1-methylazetidin-3-yl)pyridin-2-ylamino)pyridin-2(1H)-one (172a) (216 mg, 0.6 mmol), 230a (390 mg, 0.8 mmol), 1,2-dimethoxyethane (8 mL) and 1M aqueous sodium carbonate (2 mL). After bubbling N2 for 15 min, Pd(PPh3)4 (36 mg, 0.03 mmol) was added. The mixture was heated in microwave to 130° C. for 15 min. After this time, ethyl acetate (5 mL) and water (5 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×5 mL). The combined organics were washed with brine (10 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with a gradient of methylene chloride-9:1 methylene chloride:methanol to afford a 30% yield (120 mg) of 271a.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08618107B2 |
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| Source dataset | uspto-grants-2013_12 |
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| ORD ID | ord-985bb875063846b5afef2758b0f2e27f |
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| Source note | uspto-grants-2013_12 |
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