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

HRID 1831504노트

반응식

HRID 1831504 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 18180031Water 1,2-dimethoxyethane용매

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-08f37e7bfc5e4dfd89b42ba44dc1aca4
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067658B2

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