HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1507605Generated: November 1, 2026
Benzophenone imine → 1-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one
https://huagongshe.com/reaction/1507605
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzophenone imine | HCID 136809 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 6-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one | HCID 90047506 | — |
| Catalyst | Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1) | HCID 11029508 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 1-Cyclopropyl-6-(diphenylmethyleneamino)-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one | HCID 90047568 | — |
Reaction Steps
To a suspension of 6-chloro-1-cyclopropyl-3,3-dimethyl-1H-pyrrolo[3,2-c]pyridin-2(3H)-one (1.789 g, 7.56 mmol), diphenylmethanimine (2.05 g, 1.9 ml, 11.3 mmol, Eq: 1.5) and sodium tert-butoxide (1.23 g, 12.8 mmol) in toluene (48 ml) were added tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (156 mg, 151 mol) and BINAP (94.1 mg, 151 mol). The reaction mixture was heated to 100° C. for 18 hours and then diluted with dichloromethane. Silica gel was added and the solvent was evaporated. The crude material was purified by flash chromatography on silica gel using heptane/EtOAc as eluent. The title compound was obtained as brown crystals (2.31 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09221816B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-0a8c236c365f44ffa09cc015dfbee393 |
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| Source note | uspto-grants-2015_12 |
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