Diisopropylethylamine → Ethyl [4-({(2-methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate

HRID 1269607노트

반응식

HRID 1269607 반응식
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1.Br[CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:26]([CH3:37])[CH:25]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][N:5]([CH2:23][C:24]1[CH:36]=[CH:35][C:27]([O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:26]([CH3:37])[CH:25]=1)[C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 18448419N-(2-Methoxyethyl)-N-[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amineHCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

생성물 1

HCID 58622889Ethyl [4-({(2-methoxyethyl)[4'-(trifluoromethyl)-1,1'-biphenyl-3-yl]amino}methyl)-2-methylphenoxy]acetate수율 52.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of N-(2-methoxyethyl)-N-[4′-(trifluoromethyl)-1,1′-biphenyl-3-yl]amine (0.1 g, 0.34 mmol) in anhydrous acetonitrile (10 mL) was added ethyl [4-(bromomethyl)-2-methylphenoxy]acetate (0.097 g, 0.34 mmol) and N,N-diisopropylethylamine (0.059 mL, 0.34 mmol). The resulting mixture was heated to reflux and stirred under nitrogen for 3 h. The reaction mixture was concentrated in vacuo and the residue partitioned between water (20 mL) and CH2Cl2 (40 mL), the organic extract was separated by hydrophobic frit and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 12 g) eluting 9:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (90 mg).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue partitioned between water (20 mL) and CH2Cl2 (40 mL)
  5. extractionthe organic extract
  6. customwas separated by hydrophobic frit
  7. customthe solvents removed in vacuo
  8. customPurification by Biotage™ chromatography (Silica, 12 g)
  9. washeluting 9:1 cyclohexane

출처 및 근거

ORD 기록
ord-028fda1a51604d71b9a2e00b71935d58
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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