HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1696207Generated: October 31, 2026
N-Methylcyclohexylamine → N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine
https://huagongshe.com/reaction/1696207
Participants
| Role | Name | HCID | Charge |
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| Reactant | N-Methylcyclohexylamine | HCID 7514 | — |
| Reactant | Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphine | HCID 21081571 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 4-Chloro-5-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine | HCID 53438251 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine | HCID 67278086 | — |
Reaction Steps
A mixture of 4-chloro-5-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (250 mg), N-methylcyclohexanamine (306 μl), Pd(OAc)2(17 mg), sodium tert-butoxide (176 mg), 2-dicyclohexylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (73 mg) and 1,4-dioxane (2.5 mL) was evacuated and backfield with N2 three times, then degassed with N2 for 10 minutes. The mixture was heated at 100° C. for 2.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated. Purification of the crude product by column chromatography (silica gel, n-hexane:EtOAc=1:50) afforded N-cyclohexyl-5-fluoro-N-methyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-4-amine (53 mg) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08163767B2 |
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| Source dataset | uspto-grants-2012_04 |
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| ORD ID | ord-68073a08ca904e9a974dca3ee63f2326 |
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| Source note | uspto-grants-2012_04 |
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