Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | HCID 49778979 | HCID 49778979 | — |
| Reactant | HCID 178418361 | HCID 178418361 | — |
| Catalyst | Palladium hydroxide | HCID 9942167 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 49779046 | HCID 49779046 | 98% |
Reaction Steps
Palladium hydroxide (36 mg) was added to a solution of 4-(4-((6-chloroimidazo[1,2-b]pyridazin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (180 mg, 0.37 mmol) and diethyl amine (28 mg, 0.37) in methanol (25 ml) at RT under an atmosphere of nitrogen. The nitrogen atmosphere was exchanged for hydrogen and was stirred at RT for 2 h (the reaction was monitored by TLC). The compound was filtered through a bed of Celite® bed washing with methanol. The filtrate was concentrated under reduced pressure to afford 4-(4-(imidazo[1,2-b]pyridazin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (160 mg, 96.7%,) as a white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.45 (s, 1H), 8.4 (s, 1H) 8.15 (d, 1H), 7.55 (d, 2H), 7.25 (d, 1H), 7.15 (d, 2H), 7.1 (d, 2H), 7.0 (d, 2H), 5.25 (s, 2H) 3.8 (s, 3H), 1.25 (s, 6H). MS: [M+H]+: m/z=442.3. HPLC: (97.4%, Condition-A).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08946222B2 |
|---|
| Source dataset | uspto-grants-2015_02 |
|---|
| ORD ID | ord-d03162499e4d478da80f60c02cf216fc |
|---|
| Source note | uspto-grants-2015_02 |
|---|