Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | 5-Bromo-1-methyl-3-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)pyridin-2(1H)-one | HCID 58043645 | — |
| Reactant | (2-{4,4-Dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl Acetate | HCID 67016224 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68096430 | HCID 68096430 | 52.3% |
Reaction Steps
A sealed tube was charged with the mixture of 5-bromo-1-methyl-3-(5-(1-methylpiperidin-4-yl)pyridin-2-ylamino)pyridin-2(1H)-one 130c (400 mg, 1.0 mmol), (4-fluoro-2-{6-oxo-8-thia-5-azatricyclo[7.4.0.02,7]trideca-1(9),2(7)-dien-5-yl}-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate 247b (534 mg, 1.0 mmol), Pd(dppf)Cl2 (87 mg, 0.1 mmol), K3PO4.3H2O(569 mg, 2.0 mmol), and NaOAc (175 mg, 2.0 mmol) in CH3CN (20 mL). The system was evacuated and then refilled with N2. And the reaction mixture was heated at 110° C. for 2 h. Then, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography eluting with 10:1 methylene chloride/methanol to give 267a as a brown solid (350 mg, 49%). MS: [M+H]+ 670.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08618107B2 |
|---|
| Source dataset | uspto-grants-2013_12 |
|---|
| ORD ID | ord-d30d09a701b04171877d02c2aa693620 |
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| Source note | uspto-grants-2013_12 |
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