Water → 2-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridine

HRID 1831504ノート

反応式

HRID 1831504 の反応式
[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1B(O)O.CCOC(C)=O.O>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>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:23]2[CH:22]=[CH:21][C:20]([Cl:19])=[CH:25][C:24]=2[Cl:26])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2734659(2,4-Dichlorophenyl)boronic acidHCID 220520652-(Benzyloxy)-4-chloro-3-nitropyridine

生成物 1

HCID 220521282-(Benzyloxy)-4-(2,4-dichlorophenyl)-3-nitropyridine収率 82%

試薬・触媒・溶媒 2

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

実験手順

To a solution of 2-benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et. al. WO 99/01454, which is incorporated herein by reference)(5 g, 18.9 mmol) in DME/H2O, was added 2,4-dichlorophenylboronic acid (3.60 g, 18.9 mmol), Ba(OH)2 0.8H2O (5.96 g, 18.9 mmol), and Pd(PPh3)2Cl2 (0.77 g, 1.09 mmol) and the mixture was heated at reflux for 5 h. The reaction was cooled and poured into EtOAc and H2O (500 mL). The EtOAc layer was washed with H2O, brine, dried (Na2SO4), filtered and concentrated in vacuo. Purification using flash chromatography (10% EtOAc-Hexane) gave 5.79 g (82%) of 2-benzyloxy-4-(2,4-dichloro-phenyl)-3-nitro-pyridine as a viscous oil: crude MS (AP) m/z 375.2 [(M+H)+, 100].

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 h
  3. temperatureThe reaction was cooled
  4. washThe EtOAc layer was washed with H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification

出典と根拠

ORDレコード
ord-08f37e7bfc5e4dfd89b42ba44dc1aca4
出典データセット
uspto-grants-2006_06
特許番号
US07067658B2

反応ノート

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