Dichloromethane → HCID 59238889, Verbindung

HRID 2060988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060988
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])=[C:8]3[NH:21][C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][C:27]=4[C:7]3=[CH:6][C:5]2=1.[Br:29]Br.C(Cl)Cl>CN(C=O)C>[Br:29][C:6]1[C:7]2[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([F:28])[CH:26]=3)[NH:21][C:8]=2[C:9]([O:15][CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])=[C:10]2[NH:11][C:12]3[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=3[C:5]=12

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 24408BromineHCID 45138929HCID 45138929, Verbindung

Produkt 1

HCID 59238889HCID 59238889, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(2,10-difluoro-5,7-dihydroindolo[2,3-b]carbazol-6-yloxy)-N,N-dimethylethanamine (213.9 mg, 0.5638 mmol) in DMF (20 mL) at 0° C. was added Br2 in CH2Cl2 (50 mg/mL, 1.982 mL, 0.6201 mmol). The reaction was warmed to room temperature and stirred for two hours. DMF was removed via vacuum pump. The residue was dissolved in ethyl acetate (100 mL) and washed with saturated aq. NaCO3. The organic layers was concentrated and subjected to flash chromatography to provide the title compound (188.4 mg, 73%). 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.89 (br s, 2H), 8.39 (dd, J=10.0, 2.4 Hz, 2H), 7.55 (dd, J=8.8, 4.4 Hz, 2H), 7.31 (td, J=8.8, 2.4 Hz, 2H), 4.34 (t, J=5.2 Hz, 2H), 2.74 (t, J=5.6 Hz, 2H), 2.36 (s, 6H); MS (ESI) m/z 456.1 (M−H)−; MS (ESI) m/z 458.0 (M+H)+

Aufarbeitung

  1. customDMF was removed via vacuum pump
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with saturated aq. NaCO3
  4. concentrationThe organic layers was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-88649d70d4924cdcad4be2332dbdda71
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278341B2

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