1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-one

HRID 227133ノート

反応式

HRID 227133 の反応式
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([Mg]Br)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]>C1COCC1>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][N:10]=3)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:31]3[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[C:33]([O:34][CH3:35])[CH:32]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

参加物

4

反応物 2

HCID 577545871-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideHCID 178491916HCID 178491916、化合物

生成物 1

HCID 577546341-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-one収率 18.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Experimental conditions analogous to those described for Step 6 of Example 60, from 100 mg (0.248 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide in THF 2 ml, was added 1.09 ml (0.545 mmol) 3,4-dimethoxyphenylmagnesium bromide. The reaction mixture was stirred at room temperature for 30 min, then quenched with saturated solution of NH4Cl, extracted with ethyl acetate and purified with flash chromatography to give the desired product 22 mg. LCMS observed for (M+H)+: 480.

後処理

  1. customquenched with saturated solution of NH4Cl
  2. extractionextracted with ethyl acetate
  3. custompurified with flash chromatography

出典と根拠

ORDレコード
ord-ff776be363784da2a99a419d704eaf53
出典データセット
uspto-grants-2009_07
特許番号
US07557213B2

反応ノート

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