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 508034ノート

反応式

HRID 508034 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-9dd6a26878ed4ca7983b691c719db763
出典データセット
uspto-grants-2010_08
特許番号
US07786165B2

反応ノート

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