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

HRID 502246Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 502246
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6344DichloromethaneLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7427fe0c2a6f404ab1afc8a7ad10eba2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772271B2

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