Water → 6-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester

HRID 1774795ノート

反応式

HRID 1774795 の反応式
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH:5]([C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18](Br)[N:17]=1)S(C1C=CC(C)=CC=1)(=O)=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:33][O:34][C:35]([C:37]1[CH:38]=[N:39][CH:40]=[C:41](B2OC(C)(C)C(C)(C)O2)[CH:42]=1)=[O:36].O>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:33][O:34][C:35]([C:37]1[CH:42]=[C:41]([C:18]2[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[O:26])[N:17]=2)[CH:40]=[N:39][CH:38]=1)=[O:36]

参加物

7

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177502573-(Methoxycarbonyl)pyridine-5-boronic acid, pinacol esterHCID 866791573-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester

生成物 1

HCID 866791606-(2-Methoxycarbonyl-vinyl)-5-nitro-[2,3']bipyridinyl-5'-carboxylic acid methyl ester収率 99.9%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
120 °C

実験手順

3-(6-Bromo-3-nitro-pyridin-2-yl)-3-(toluene-4-sulfonyl)-propionic acid methyl ester (1.2 g, 2.7 mmol), Pd(PPh3)2Cl2 (190 mg, 0.27 mmol), Na2CO3 (572 mg, 5.4 mmol) and 3-(methoxycarbonyl)pyridine-5-boronic acid pinacol ester (926 mg, 3.5 mmol) were dissolved in 1,4-dioxane (4.0 mL) and the resulting reaction mixture was heated at 120° C. for 3 hours before it was poured into H2O (50 mL). After extraction with EtOAc, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give 6-(2-methoxycarbonyl-vinyl)-5-nitro-[2,3′]bipyridinyl-5′-carboxylic acid methyl ester (926 mg, quant.) as a light yellow solid. MS: 344.1 (M+H+).

後処理

  1. customthe resulting reaction mixture
  2. extractionAfter extraction with EtOAc
  3. washthe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-01f413874ecd41a8bead1a0768eafa0f
出典データセット
uspto-grants-2016_02
特許番号
US09260408B2

反応ノート

読み込み中…