4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehyde → Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate

HRID 508034노트

반응식

HRID 508034 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=1.[CH2:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=O)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:17]>C1(C)C=CC=CC=1>[CH2:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:4]([F:15])[CH:3]=3)[CH:30]=2)=[C:24]([CH3:37])[CH:23]=1)[CH3:17]

참가 물질

4

반응물 2

HCID 231117224'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-carbaldehydeHCID 23157234Ethyl 3-(4-amino-2-fluorophenyl)propanoate

생성물 1

HCID 23157676Ethyl 3-[4-({[4'-(2-ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoate수율 83.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

To a solution of ethyl 3-(4-amino-2-fluorophenyl)propanoate (1.48 g, 7.00 mmol) and 4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-carbaldehyde (2.09 g, 7.00 mmol) in toluene (15 mL) were added molecular sieves (0.4 nm, beads, 3.5 g), and the mixture was stirred at room temperature for 30 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in ethanol (20 mL), 10% palladium-carbon (50% water-containing product, 0.5 g) was added, and the mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 12 hr. The catalyst was filtered off, and the obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane) to give the title compound (2.88 g, yield 83%) as a colorless oil.

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. dissolutionThe obtained residue was dissolved in ethanol (20 mL)
  4. addition10% palladium-carbon (50% water-containing product, 0.5 g) was added
  5. stirringthe mixture was stirred under a hydrogen atmosphere (balloon pressure) at room temperature for 12 hr
  6. filtrationThe catalyst was filtered off
  7. concentrationthe obtained filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (5%-30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-9dd6a26878ed4ca7983b691c719db763
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

반응 노트

불러오는 중…