HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1878722Generated: October 31, 2026
1,10-Phenanthroline → tert-Butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate
https://huagongshe.com/reaction/1878722
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,10-Phenanthroline | HCID 1318 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Iodo-7-methoxyquinoline | HCID 17750651 | — |
| Reactant | tert-Butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate | HCID 69231018 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | tert-Butyl 1-(1-(7-methoxyquinolin-4-yloxy)-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate | HCID 59843045 | — |
Reaction Steps
A suspension of tert-butyl 1-(1-hydroxy-2-methylpropan-2-yl)-6-oxo-1,6-dihydropyridin-3-ylcarbamate (275 mg, 974 μmol), 1,10-phenanthroline (35 mg, 195 μmol), cesium carbonate (635 mg, 1948 μmol), copper(I) iodide (19 mg, 97 μmol), and 4-iodo-7-methoxyquinoline in DMF (4 mL) was heated to 100° C. for 2 h. The reaction mixture was partitioned between CH2Cl2 (50 mL) and 5% NaHCO3 (25 mL). The aqueous was extracted twice with CH2Cl2 (5 mL). The combined extracts were concentrated onto dry silica (10 g) and purified on 80 grams of silica eluting with 0-6% 2M NH3 in MeOH/CH2Cl2. MS (ESI pos. ion) m/z (MH+): 440. Calc'd exact mass for C24H29N3O5: 439.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08314087B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-f10c821af45d41aa825a3b34dc1c68b3 |
|---|
| Source note | uspto-grants-2012_11 |
|---|
