Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Reactant | HCID 178418416 | HCID 178418416 | — |
| Reactant | HCID 178479649 | HCID 178479649 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Product | HCID 178497287 | HCID 178497287 | — |
Reaction Steps
A mixed liquid of 7-bromo-4-fluoroisoquinolin-1-ol hydrochloride (3.0 g), palladium (II) acetate (484 mg), 1,1′-bis(diphenylphosphino)ferrocene (1.2 g), triethylamine (4.4 g), NMP (60 mL), and methanol (60 mL) was stirred at room temperature for 15 minutes while carbon monoxide gas was passed therethrough. The reaction was further heated under stirring in an oil bath at 80° C. for 16 hours under a carbon monoxide gas atmosphere at 1 atm. The reaction mixture was returned to room temperature, the insoluble materials were separated by filtration, and then the precipitate was concentrated under reduced pressure. The resulting residue was diluted with water, and then the precipitate was collected by filtration to obtain methyl 4-fluoro-1-hydroxyisoquinoline-7-carboxylate (2.3 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08853242B2 |
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| Source dataset | uspto-grants-2014_10 |
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| ORD ID | ord-9849db07da1f4c918176d22222fc9e05 |
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| Source note | uspto-grants-2014_10 |
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