HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 874666Generated: October 30, 2026
Sodium Carbonate → 5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)-2-pyridylamine
https://huagongshe.com/reaction/874666
Participants
| Role | Name | HCID | Charge |
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| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine | HCID 2756555 | — |
| Reactant | 6-Bromo-7-methyl-2,3-dihydro-1,4-benzodioxine | HCID 12464549 | — |
| Catalyst | Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) | HCID 11714597 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-(7-methyl-2H,3H-benzo[e]1,4-dioxin-6-yl)-2-pyridylamine | HCID 58487373 | 26% |
Reaction Steps
The 2-aminopyridine-5-boronic acid pinacol ester (400 mg, 1.8 mmol) and 182 (550 mg, 2 mmol) was dissolved in 2 mL 1,4-dioxane and 2 mL MeCN. The 4 ml of 2 M Na2CO3 was added and the mixture was bubbled with Ar for 2 min before bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (A-Phos, 70 mg, 0.1 mmol) was added. The reaction was heated at 85° C. for 2 h. The reaction mixture was worked-up with EtOAc extraction. The product was purified by flash column and afforded 183 (112.4 mg, 26%) as yellow oil. LC-MS: calcd. for C14H14N2O2: 243 (M+1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08980629B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-4991d9ac135b4947b7d28eafb069a11d |
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| Source note | uspto-grants-2015_03 |
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