HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1918856Generated: November 2, 2026
1,2-Dimethoxyethane → HCID 67016116, compound
https://huagongshe.com/reaction/1918856
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-(2-(Acetoxymethyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-1(2H)-one | HCID 58043877 | — |
| Reactant | 5-Bromo-3-(5-(3-hydroxyazetidin-1-yl)pyridin-2-ylamino)-1-methylpyridin-2(1H)-one | HCID 58043923 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67016116 | HCID 67016116 | 30.1% |
Reaction Steps
A microwave tube equipped with a magnetic stirrer was charged with 128c (220 mg, 0.6 mmol), 2-(1-oxo-3,4,6,7,8,9-hexahydropyrazino[1,2-a]indol-2(1H)-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl acetate 114a (350 mg, 0.8 mmol), DME (7 mL) and 1M aqueous sodium carbonate (1.9 mL). After bubbling N2 for 15 min, Pd(PPh3)4 (36 mg, 0.03 mmol) was added. The mixture was heated in microwave to 135° C. for 15 min. After this time, ethyl acetate (10 mL) and water (10 mL) were added. The separated aqueous layer was extracted with ethyl acetate (2×10 mL). The combined organics were washed with brine (20 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography eluting with a gradient of CH2Cl2-60:35:5 CH2Cl2:diethyl ether:MeOH to afford a 30% yield (110 mg) of 128d.
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-5037bc6ce26e4db58066e79571e39a67 |
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| Source note | uspto-grants-2013_12 |
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