Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Tolylboronic acid | HCID 79799 | — |
| Reactant | 7-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one | HCID 11789822 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Ethylene Glycol | HCID 174 | — |
| Product | HCID 22172943 | HCID 22172943 | 95.2% |
Reaction Steps
Using a method similar to Example 16 d), 3.61 g (0.020 mol) of (1), 3.0 g (0.022 mol) of 4-methylphenylboronic acid, 4.66 g (0.044 mol) of sodium carbonate were placed in 60 ml of ethylene glycol/12 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 22.4 mg (0.1 mmol) of palladium acetate and 0.114 g (0.2 mmol) of TMSPP, the reaction mixture was stirred for 2 hours at 125° C. After addition of 60 ml of water, the aqueous phase was extracted 4 times with 50 ml each time of ether, the combined ether phases were washed with 50 ml of water and 50 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 4.5 g of (21) as solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06963017B2 |
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| Source dataset | uspto-grants-2005_11 |
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| ORD ID | ord-abbf714f7e734e84ad4d23cfe5e72f0b |
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| Source note | uspto-grants-2005_11 |
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