Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Formate | HCID 2723810 | — |
| Reactant | HCID 86716498 | HCID 86716498 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86716499 | HCID 86716499 | 75% |
Reaction Steps
To a mixture of tert-butyl (1-{4-[3-phenyl-6-bromo-8-methoxyimidazo[1,2-b]pyridazin-2-yl]phenyl}cyclobutyl)carbamate that was prepared in a manner analgous to that described for Intermediate Example Int-7 (0.075 g, 0.14 mmol) and 5% palladium on carbon (0.007 g) in DMF (1 mL) was added a solution of sodium formate (0.074 g, 1.09 mmol, 8.0 eq) in water (0.2 mL). The resulting mixture was stirred at 80° C. for 3 h, diluted with MeOH (10 mL) and stirred at room temperature for 1 h. The resulting solution was filtered through a membrane filter, and the solids were washed with MeOH (1 mL). The resulting solution was diluted with EtOAc (25 mL), washed with water (2×25 mL), dried (Na2SO4 anh.) and concentrated under reduced pressure to give tert-butyl {1-[4-(8-methoxy-3-phenylimidazo[1,2-b]pyridazin-2-yl)phenyl]cyclobutyl}carbamate approximately 75% purity (0.058 g, 90%):
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09206185B2 |
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| Source dataset | uspto-grants-2015_12 |
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| ORD ID | ord-4be47b5e5abd47138897acdd31bd8f17 |
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| Source note | uspto-grants-2015_12 |
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