Ethyl 2,6-dichloro-4-phenylquinoline-3-carboxylate → HCID 86682959, compound

HRID 1497103Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2].[CH:24]1([Mg]Br)[CH2:28][CH2:27][CH2:26][CH2:25]1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]([Cl:22])=[CH:11][CH:10]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 2,6-dichloro-4-phenyl-quinoline-3-carboxylic acid ethyl ester (prepared as described in example 11 step B, 100 mg, 0.29 mmol) in 2 ml THF, was added cyclopentyl magnesium bromide (2 M solution in diethyl ether) (0.72 ml, 1.44 mmol) drop wise at 25° C. under nitrogen. The resulting reaction mixture was stirred for 40 min at 50° C. in a microwave. The reaction mixture was then quenched with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The combined organic phases were dried over anhydrous sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (2% ethyl acetate in hexane) to afford 6-chloro-2-cyclopentyl-4-phenyl-quinoline-3-carboxylic acid ethyl ester (16.5 mg, 15%) as pale yellow sticky solid. LC-MS: 380 (M+H)+.

Workup

customThe resulting reaction mixture
customThe reaction mixture was then quenched with saturated aqueous NH4Cl solution
extractionextracted with ethyl acetate
dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customto give a crude residue which
customwas purified by flash column chromatography (2% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-e7b0f0bf3d0e43e79e3ce58cd4d022dd
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199938B2

Reaction notes

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