Tetrahydrofuran → 3-(6-Cyano-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

HRID 2215773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215773
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]([NH2:14])=[O:13])[CH:4]=[CH:3]1.C[O:16][C:17](=O)[C:18]([C:20]1[C:28]2[C:23](=[CH:24][C:25]([C:29]#[N:30])=[CH:26][CH:27]=2)[NH:22][CH:21]=1)=O.CC(C)([O-])C.[K+].C1COCC1>CN(C=O)C>[C:29]([C:25]1[CH:24]=[C:23]2[C:28]([C:20]([C:18]3[C:17](=[O:16])[NH:14][C:12](=[O:13])[C:11]=3[C:9]3[CH:8]=[CH:7][CH:6]=[C:5]4[C:10]=3[N:2]([CH3:1])[CH:3]=[CH:4]4)=[CH:21][NH:22]2)=[CH:27][CH:26]=1)#[N:30]

Komponenten

6

Edukt 4

HCID 8028TetrahydrofuranHCID 114353972-(1-methyl-1H-indol-7-yl)acetamideHCID 23665647Potassium tert-butoxideHCID 69642384(6-cyano-1H-indol-3-yl)-oxo-acetic acid methyl ester

Produkt 1

HCID 219500243-(6-Cyano-1H-indol-3-yl)-4-(1-methyl-1H-indol-7-yl)-pyrrole-2,5-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 2-(1-methyl-1H-indol-7-yl)-acetamide (0.410 g, 2.18 mmol) and (6-cyano-1H-indol-3-yl)-oxo-acetic acid methyl ester (0.480 g, 2.10 mmol) in DMF (30 mL) under N2 was added a 1.0 M solution of potassium-tert-butoxide in THF (7.6 mL, 7.6 mmol) dropwise over 5 minutes. The mixture was heated at 70° C. for 17 h. The mixture was cooled to room temperature, quenched with 1N HCl (excess) and poured into EtOAc. The organic layer was separated, washed with water (3×), saturated aq NaHCO3, and brine, dried (MgSO4), filtered and concentrated onto flash SiO2. Flash chromatography (60–70% EtOAc/hex) gave the title compound as a bright orange-red solid which was dried under vacuum at 75° C. overnight (0.416 g, 54%). 1H NMR (400 MHz, DMSO-d6) 12.29 (br s, 1H), 11.26 (s, 1H), 8.03 (d, J=2.3 Hz, 1H), 7.86 (br s, 1H), 7.63 (d, J=8 Hz, 1H), 7.25 (d, J=3 Hz, 1H), 6.99 (dd, J=8, 8 Hz, 1H), 6.91 (d, J=8 Hz, 1H), 6.89 (d, J=8 Hz, 1H), 6.60 (d, J=8 Hz, 1H), 6.49 (d, J=3 Hz, 1H), 3.66 (s, 3H). IR (KBR, cm−1) 3282, 2223, 1751, 1698. MS (electrospray, m/z) 367.1 (M++1), 365.2 (M−−1). HRMS 367.1190 (M++1, calcd for C22H15N4O2 367.1195).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. customquenched with 1N HCl (excess)
  3. additionpoured into EtOAc
  4. customThe organic layer was separated
  5. washwashed with water (3×), saturated aq NaHCO3, and brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated onto flash SiO2

Quellen und Nachweise

ORD-Eintrag
ord-3eede39ea4314d2997e960f1a1b66f39
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109229B2

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