Phenylboronic Acid → 3-(1-Benzyl-2-methyl-6-phenyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

HRID 1466774

反応式

HRID 1466774 の反応式
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16](Br)=[CH:17][CH:18]=3)[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[CH3:28])[CH:5]=1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C([O-])(O)=O.[Na+]>COCCOC.O.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>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:17][CH:18]=3)[N:13]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:12]=2[CH3:28])[CH:5]=1

参加物

6

反応物 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 667652363-(1-Benzyl-6-bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

生成物 1

HCID 667652333-(1-Benzyl-2-methyl-6-phenyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 18180031Water 1,2-dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

3-(1-Benzyl-6-bromo-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.080 g, 0.17 mmol), phenylboronic acid (0.042 g, 0.34 mmol), NaHCO3 (0.073 g, 0.85 mmol) and bis(triphenylphosphine)palladium(II) dichloride (0.012 g, 0.02 mmol) were suspended in DME:H2O (1:1, 3 mL) and the reaction vessel was purged with N2 (g). The reaction was heated to 90° C. and after two hours the mixture was submitted to aqueous workup then purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound.

後処理

  1. customthe reaction vessel was purged with N2 (g)
  2. customthen purified by silica gel chromatography (0-30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a64ee6bcc6c34e89bc9d7a766262aa0e
出典データセット
uspto-grants-2015_04
特許番号
US09000025B2

関連ノート

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