HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 2-(trans)-{3'-[3-[(Cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-yl}cyclopropanecarboxylic Acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Naphthyridinone | HCID 11386747 | — |
| Reactant | 2-(trans)-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxylic Acid | HCID 67494736 | — |
| Reactant | Dimethylformamide n-propanol | HCID 86598119 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | 2-(trans)-{3'-[3-[(Cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-yl}cyclopropanecarboxylic Acid | HCID 56679969 | — |
Reaction Steps
A mixture of NAPHTHYRIDINONE 2 (1.0 eq), acid from step 3 (1.5 eq), Na2CO3 (3.5 eq; 2M in H2O), Pd(OAc)2 (0.05 eq.) and PPh3 (0.15 eq.) or PdCl2dppf (0.05 eq) in n-propanol-DMF (1:1, 0.1M) was stilled at 70° C. for 2 h. The mixture was cooled to it, quenched with AcOH and diluted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc, 60:40, 2% AcOH) afforded the title compound as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07238706B2 |
| Source dataset | uspto-grants-2007_07 |
| ORD ID | ord-d5efbfcb867743e58aa80a770d911435 |
| Source note | uspto-grants-2007_07 |