Reacción #80732

ord-f573eba3c4f04e5d987a05000aaa80d9

Ecuación de reacción

[H-].[Na+]
NaH
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
ethyl 4-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl) ethynyl benzoate
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
Compound 4
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate
BrCc1ccccc1
benzyl bromide
O=C([O-])c1ccccc1
Compound 5
O=C([O-])c1ccccc1
benzoate
→
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(=O)N3Cc2ccccc2)cc1
title compound
CCOC(=O)c1ccc(C#Cc2ccc3c(c2)C(C)(C)CC(=O)N3Cc2ccccc2)cc1
Ethyl 4- [(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-benzyl-6-quinolinyl)ethynyl]benzoate

Reactantes

[H-].[Na+]
NaH
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
ethyl 4-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl) ethynyl benzoate
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
Compound 4
CC1(C)CC(=O)Nc2ccc(C#Cc3ccc(C(=O)[O-])cc3)cc21
4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl)ethynyl]benzoate
BrCc1ccccc1
benzyl bromide
—
ethyl
O=C([O-])c1ccccc1
Compound 5
O=C([O-])c1ccccc1
benzoate

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

NaH (93.6 mg, 2.6 mmol), ethyl 4-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-6-quinolinyl) ethynyl benzoate (Compound 4, 604 mg, 1.7 mmol) and benzyl bromide (2.06 mL, 17 mmol) in 3 mL of DMF were reacted substantially in accordance with the procedure used for the preparation of ethyl 4-[(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-(1-iso-propyl-6-quinolinyl)ethynyl]benzoate (Compound 5), to yield the title compound as white solids (744 mg).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05616712uspto-grants-1997_04