Sodium Bicarbonate → 1-Acetyl-2,3-dihydro-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

HRID 273854ノート

反応式

HRID 273854 の反応式
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH2:18])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH2:30][C:31]([F:34])([F:33])[F:32].C(=O)(O)[O-].[Na+]>C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH:18][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 516892Sodium BicarbonateHCID 200943331-Acetyl-5-(2-aminopropyl)-2,3-dihydro-1H-indole-7-carbonitrileHCID 200943351-(2-Bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene

生成物 1

HCID 200943401-Acetyl-2,3-dihydro-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile収率 56.2%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C.

後処理

  1. customthe mixture was reacted in a sealed tube at 95° C. for 12 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  4. additiona mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent
  5. customrecrystallized from diethyl ether-hexane

出典と根拠

ORDレコード
ord-1cee60b0311d4c5f8ca5695401856b11
出典データセット
uspto-grants-1995_02
特許番号
US05387603

反応ノート

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