Potassium Carbonate → 7-chloro-3-(4-methoxycarbonyl-2-oxo-2H-pyridin-1-ylmethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester

HRID 1261783

反応式

HRID 1261783 の反応式
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15]Br)=[CH:11][CH:10]=[C:9]([Cl:18])[CH:8]=2)=[O:4].[CH3:25][O:26][C:27](=[O:35])[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([OH:34])[CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]2[C:12]([C:13](=[O:17])[C:14]=1[CH2:15][N:31]1[CH:32]=[CH:33][C:28]([C:27]([O:26][CH3:25])=[O:35])=[CH:29][C:30]1=[O:34])=[CH:11][CH:10]=[C:9]([Cl:18])[CH:8]=2)=[O:4]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 86672058Methyl 3-(bromomethyl)-7-chloro-4-oxo-1-phenyl-1,4-dihydroquinoline-2-carboxylateHCID 178498433HCID 178498433、化合物

生成物 1

HCID 708168387-chloro-3-(4-methoxycarbonyl-2-oxo-2H-pyridin-1-ylmethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester収率 46.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 3-bromomethyl-7-chloro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (550 mg, 1.35 mmol), methyl-2-hydroxyisonicotinate (290 mg, 1.89 mmol) and potassium carbonate (280 mg, 2.03 mmol) in N,N-dimethylformamide (15 mL) was stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. Flash chromatography (ISCO column, 40% ethyl acetate/hexanes) afforded 7-chloro-3-(4-methoxycarbonyl-2-oxo-2H-pyridin-1-ylmethyl)-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid methyl ester (300 mg, 46%) as a white solid. MS m/e calcd for C25H19ClN2O6 [(M+H)+] 479.0. Found 479.0.

後処理

  1. concentrationAt this time, the reaction was concentrated in vacuo

出典と根拠

ORDレコード
ord-9d5db74205f34643b051a3fe1b73c214
出典データセット
uspto-grants-2013_06
特許番号
US08471027B2

関連ノート

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