HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 513064Generated: October 25, 2026
Nitrogen → 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine
https://huagongshe.com/reaction/513064
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| Reactant | 6-Chloro-2-iodopyridin-3-amine | HCID 18407043 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 6-Chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine | HCID 57908159 | 88% |
Reaction Steps
To a solution of 6-chloro-2-iodo-pyridin-3-ylamine (16.0 g, 62.7 mmol) in toluene (160 mL) and water (80 mL) were added Et3N (12.7 g, 125 mmol), Pd(PPh3)2Cl2 (2.2 g, 3.1 mmol), CuI (238 mg, 1.3 mmol) and 3,3-dimethyl-but-1-yne (7.7 g, 94 mmol) successively under N2 atmosphere. The reaction mixture was heated at 70° C. for 3 hours and was allowed to cool to room temperature. The resulting mixture was extracted with ethyl acetate (150 mL×3). The combined organic extracts were dried over anhydrous Na2SO4 and evaporated under vacuum to give 6-chloro-2-(3,3-dimethyl-but-1-ynyl)-pyridin-3-ylamine (11.5 g, 88%), which was used in the next step without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09102672B2 |
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| Source dataset | uspto-grants-2015_08 |
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| ORD ID | ord-29912d0aa2fd4ab58c1462a8712a01bd |
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| Source note | uspto-grants-2015_08 |
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