HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1392722Generated: November 3, 2026
Sodium Carbonate → ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate
https://huagongshe.com/reaction/1392722
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 3'-[3-[(Cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]-1,1'-biphenyl-4-carboxylic Acid | HCID 10025432 | — |
| Reactant | Ethyl 1-(4-bromobenzyl)cyclobutanecarboxylate | HCID 69158278 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide n-propanol | HCID 86598119 | — |
| Product | ethyl 1-({3'-[3-[(cyclopropylamino)carbonyl]-4-oxo-1,8-naphthyridin-1(4H)-yl]biphenyl-4-yl}methyl)cyclobutanecarboxylate | HCID 69158192 | — |
Reaction Steps
A mixture of NAPHTHYRIDNONE 3 (1.0 eq), ester from step 1 (1.5 eq), Na2CO3 (3.5eq; 2M in H2O), Pd(OAc)2 (0.05eq.) and PPh3 (0.15eq.) or PdCl2dppf (0.05 eq) in n-propanol-DMF (1:1, 0.1M) was stirred at 70° C. for 2 h. The mixture was cooled to rt, quenched with AcOH and diluted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (CH2Cl2/MeOH, 99:1) afforded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07342024B2 |
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| Source dataset | uspto-grants-2008_03 |
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| ORD ID | ord-eaaad3d4f83545049907e56012a1cf8a |
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| Source note | uspto-grants-2008_03 |
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