Tetrahydrofuran → HCID 178471914, compound

HRID 226931Notes

Reaction equation

HRID 226931 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([C:10](Cl)=[O:11])=[N:7][C:8]=1[CH3:9].[CH2:13]([O:15][C:16](=[O:26])[CH:17]=[CH:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:14].[H-].[Na+].O1CCCC1>CCCCCC.C(OCC)(=O)C>[CH2:13]([O:15][C:16](=[O:26])[C:17]([C:10]([C:6]1[CH:5]=[CH:4][C:3]([CH3:2])=[C:8]([CH3:9])[N:7]=1)=[O:11])=[CH:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:14]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 668793173-Phenylamino-acrylic acid ethyl esterHCID 86613646HCID 86613646, compound

Product 1

HCID 178471914HCID 178471914, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound 2e was prepared following the procedure outlined in Step 1 of Example 6 using 2.28 g (11.0 mmol) of 5,6-dimethyl-pyridine-2-carbonyl chloride hydrochloride (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351), 1.91 g (10.0 mmol) of 3-phenylamino-acrylic acid ethyl ester, 1.08 g (27.0 mmol) of 60% sodium hydride and 25 mL tetrahydrofuran. Flash chromatography using 10-80% ethyl acetate in hexane yielded 575 mg of the product as yellow solid. LC-MSD, m/z for C19H20N2O3 [M+H]+=325.5, HPLC retention time: 1.9 min.

Sources & evidence

ORD record
ord-8d2f88fb8d574a02b97cc613bf8169ee
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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