Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propargyl alcohol | HCID 7859 | — |
| Reactant | HCID 9955567 | HCID 9955567 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | HCID 9951891 | HCID 9951891 | 85% |
Reaction Steps
A suspension of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-cinnolinecarboxamide; (Ex. 1, 0.13 g), propargyl alcohol (0.035 mL), CuI (0.028 g), and Pd(PPh3)2Cl2 (0.013 g) in 11 mL diethylamine is stirred at room temperature for 18 h. The solid in the reaction is filtered, washed with water, and dried. The solid is dissolved in CH2Cl2 and adsorbed onto silica. Purification by chromatography (eluent CH2Cl2 (1L), 1% MeOH/CH2Cl2 (1L), 2% MeOH/CH2Cl2 (1L), 3% MeOH/CH2Cl2 (1L), 5% MeOH/CH2Cl2 (1L)) affords the desired product as a tan solid (0.094 g, 85%). Physical characteristics are as follows: m.p. 229-231° C.; 1H NMR (300 MHz, DMSO-d6) δ9.92, 8.19, 7.96, 7.40, 5.45, 4.55, 4.36, 4.24; IR (drift) 3365, 3273, 1656, 1598, 1551, 1479, 1410, 1351, 1284, 1034, 1028, 821, 812, 671, 646 cm−1; MS (ESI) m/z 382.1 (M+H)+; HRMS (FAB) calcd for C20H16ClN3O3+H1 382.0958, found 382.0963.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06624160B2 |
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| Source dataset | uspto-grants-2003_09 |
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| ORD ID | ord-dc8215d90e474895a53aefa26223087b |
|---|
| Source note | uspto-grants-2003_09 |
|---|
