Potassium Carbonate → 4-(4-(4-(Benzyloxy)phenyl)oxazol-5-yl)pyridine

HRID 33915

반응식

HRID 33915 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([N+:26]#[C-:27])S(C2C=CC(C)=CC=2)(=O)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:28](=[O:35])[C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>CO.COCCOC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:26]=[CH:27][O:35][C:28]=2[C:29]2[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 133894-PyridinecarboxaldehydeHCID 866064171-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzene

생성물 1

HCID 597974954-(4-(4-(Benzyloxy)phenyl)oxazol-5-yl)pyridine수율 84%

시약·촉매·용매 2

HCID 887Methanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 1-((4-(Benzyloxy)phenyl)isocyanomethylsulfonyl)4-methylbenzene (4.3 g, 11.4 mmol), isonicotinaldehyde (1.34 g, 12.5 mmol) and K2CO3 (3.15 g, 22.8 mmol) in methanol (96 mL ) and DME (30 mL) was heated at reflux for 5 h. After removal of solvent, the residue was purified by silica gel chromatography (2:1 hexane/EtOAc) to provide 2.29 g (84%) of a white solid. 1H NMR (400 MHz, CDCl3) δ: 5.12v (s, 2H), 7.03 (d, 2H), 7.46 (m, 6H), 7.56 (d, 2H), 7.61 (d, 2H), 8.02 (s, 1H), 8.58 (d, 2H). MS m/z: 329 [M+1]+.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 5 h
  3. customAfter removal of solvent
  4. customthe residue was purified by silica gel chromatography (2:1 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-600b1aaedd034603afd57d4f4370a05a
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429665B2

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