Water → isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester

HRID 502246노트

반응식

HRID 502246 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12][CH3:13])[CH:10]=2)[C:5]([C:14]#[N:15])=[C:4]1C1C=CC(O)=CC=1)[CH3:2].Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+]([O-])=O)=[CH:29][CH:28]=1)=[O:25].[CH:36]([NH:39][CH3:40])([CH3:38])[CH3:37].O>CCN(CC)CC.C(Cl)Cl.C(OCC)(=O)C>[C:14]([C:5]1[C:6]2[C:11](=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)[N:3]([CH2:1][CH3:2])[C:4]=1[C:30]1[CH:31]=[CH:32][C:27]([O:26][C:24](=[O:25])[N:39]([CH:36]([CH3:38])[CH3:37])[CH3:40])=[CH:28][CH:29]=1)#[N:15]

참가 물질

8

반응물 4

HCID 962WaterHCID 78485N-MethylisopropylamineHCID 821294-Nitrophenyl chloroformateHCID 594253351-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile

생성물 1

HCID 59425594isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester수율 70%

시약·촉매·용매 3

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 1-ethyl-2-(4-hydroxyphenyl)-6-methoxy-1H-indole-3-carbonitrile (58 mg, 0.2 mmol) in 4 mL of Et3N and CH2Cl2 (1/1) is added p-nitrophenyl chloroformate (100 mg, 0.5 mmol) at room temperature. After the mixture is stirred for about 1 h, N-isopropylmethylamine (0.062 mL, 0.6 mmol) is added. The mixture is stirred for 3 h and then water and ethyl acetate are added to the reaction mixture. The organic layer is separated, washed with aqueous HCl (1N) and brine, dried over anhydrous Na2SO4, and filtered and concentrated. The crude solid is purified by preparative HPLC to afford 70% of isopropyl-methyl-carbamic acid 4-(3-cyano-1-ethyl-6-methoxy-1H-indol-2-yl)-phenyl ester.

후처리

  1. stirringThe mixture is stirred for 3 h
  2. customThe organic layer is separated
  3. washwashed with aqueous HCl (1N) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude solid is purified by preparative HPLC

출처 및 근거

ORD 기록
ord-7427fe0c2a6f404ab1afc8a7ad10eba2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772271B2

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