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Dimethylformamide → N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

HRID 1250480
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HRID 1250480 반응식
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[H-].[Na+].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](Br)[N:17]=1.[CH3:25][N:26]([CH:28]=[O:29])C>CCCCCC>[C:25]1([NH:26][C:28]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=3)[N:17]=2)=[O:29])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27332613-(Trifluoromethoxy)phenolHCID 109015692,6-Dibromo-4-methoxypyridine

생성물 1

HCID 15906599N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

시약·촉매·용매 1

HCID 8058Hexane
용매

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온도
110 °C

실험 절차

2.00 g (0.00937×1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937×1.04 mol) of NaH and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110° C. for about 4 hours, the obtained mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

후처리

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the obtained solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe resultant solution was concentrated
  5. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  6. customthe obtained eluate was subjected to recrystallization

출처 및 근거

ORD 기록
ord-f679f1a0be3743e791a0679138d9e2cb
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06339045B1

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