Water → N-[3-(3'-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide

HRID 24416

反応式

HRID 24416 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[O:23][CH3:24])[CH:5]=[C:6]1[C:14]2[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:19].C(=O)([O-])[O-].[Na+].[Na+].[C:31]([NH:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][CH:40]=1)(=[O:33])[CH3:32].O>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:31]([NH:34][C:35]1[CH:40]=[C:39]([C:2]2[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[C:4]([CH:5]=[C:6]3[C:14]4[C:9](=[CH:10][C:11]([NH:15][C:16](=[O:18])[CH3:17])=[CH:12][CH:13]=4)[NH:8][C:7]3=[O:19])[CH:3]=2)[CH:38]=[CH:37][CH:36]=1)(=[O:33])[CH3:32]

参加物

8

反応物 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 157274(3-Acetamidophenyl)boronic acidHCID 54460383N-[3-(3-bromo-4-methoxybenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide

生成物 1

HCID 69763391N-[3-(3'-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide収率 43.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

Tetrakis(triphenylphosphine)palladium(0) (0.01 g) was added to a solution of N-[3-(3-bromo-4-methoxybenzylidene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide (0.14 g) in toluene (1 ml) and ethanol (1 ml) followed by addition of 2M aqueous sodium carbonate (0.72 ml). To this mixture was 3-acetylamino-phenylboronic acid (0.07 g), and the mixture was held at 100° C. in a sealed tube for 12 hours. The reaction mixture was added to water (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, dichloromethane then 5-10% methanol/dichloromethane) afforded 0.07 g (43%) of N-[3-(3′-acetylamino-6-methoxybiphenyl-3-ylmethylene)-2-oxo-2,3-dihydro-1H-indol-6-yl]-acetamide as a yellow solid. About 26% isomer by 1HNMR.

後処理

  1. extractionextracted with ethyl acetate (2×100 ml)
  2. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-082aadaa471d4039b25bf68b8860e1aa
出典データセット
uspto-grants-2005_02
特許番号
US06855730B2

関連ノート

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