Sodium hydride → 6-Chloro-4-(2-chloro-benzyl)-8-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

HRID 1497142Notes

Reaction equation

HRID 1497142 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]([NH:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([Cl:16])=[CH:11][C:10]=1[C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])=[O:7])[CH3:2].[H-].[Na+]>CS(C)=O>[CH2:1]([O:3][C:4]([C:5]1[C:6](=[O:7])[NH:8][C:9]2[C:10]([C:17]=1[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])=[CH:11][C:12]([Cl:16])=[CH:13][C:14]=2[F:15])=[O:26])[CH3:2]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86682982N-[4-Chloro-2-(2-chloro-phenylethynyl)-6-fluoro-phenyl]-malonamic acid ethyl ester

Product 1

HCID 866829836-Chloro-4-(2-chloro-benzyl)-8-fluoro-2-oxo-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared in analogy to example 29 step B from N-[4-Chloro-2-(2-chloro-phenylethynyl)-6-fluoro-phenyl]-malonamic acid ethyl ester (217 mg, 0.55 mmol) and NaH (33 mg, 0.83 mmol) in DMSO. Off white solid (120 mg, 55%). MS (ESI): 394 (M+H)+.

Sources & evidence

ORD record
ord-2994fb87b8fd4959b76032c4b21b0d41
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…