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

HRID 273854노트

반응식

HRID 273854 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-1cee60b0311d4c5f8ca5695401856b11
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387603

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