HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 87192311, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1-(Benzenesulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 44755203 | — |
| Reactant | 4-(5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-6-chloro-N-cyclohexylpyridin-2-amine | HCID 86649871 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 87192311 | HCID 87192311 | 56.3% |
Reaction Steps
A solution of Example 171a (0.158 g, 0.29 mmol), 1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.100 g, 0.29 mmol), catalytic amount of [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II), complex with dichloromethane (1:1) and saturated sodium bicarbonate solution (2 mL) in 8 mL dimethylformamide was heated at 65° C. for 2 hours. The material was cooled to room temperature, diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified on silica gel using flash chromatography (20% ethyl acetate/hexane) to afford 0.11 g of the title compound. m/z 673.6 (ESI, M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08435980B2 |
| Source dataset | uspto-grants-2013_05 |
| ORD ID | ord-67b794a91b3c4ad4967693a19fa83e61 |
| Source note | uspto-grants-2013_05 |