Triethylamine → 3-[2-(Trimethylsilyl)ethoxycarbonylamino]-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

HRID 2217755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217755
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.C([C:21]1[N:36]=[CH:35][C:24]2[N:25]([CH:32]([CH3:34])[CH3:33])[C:26]3[C:31]([C:23]=2[C:22]=1[CH2:37][CH3:38])=[CH:30][CH:29]=[CH:28][CH:27]=3)(O)=O.C([N:41]([CH2:44]C)CC)C.[CH3:46][Si:47]([CH3:52])([CH3:51])[CH2:48][CH2:49][OH:50]>C1(C)C=CC=CC=1>[CH3:46][Si:47]([CH3:52])([CH3:51])[CH2:48][CH2:49][O:50][C:44]([NH:41][C:21]1[N:36]=[CH:35][C:24]2[N:25]([CH:32]([CH3:34])[CH3:33])[C:26]3[C:31]([C:23]=2[C:22]=1[CH2:37][CH3:38])=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:8]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 180132-(Trimethylsilyl)ethanolHCID 199401P,P-Diphenylphosphinic azideHCID 693095113-Carboxy-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole

Produkt 1

HCID 693078183-[2-(Trimethylsilyl)ethoxycarbonylamino]-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indoleAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Diphenyl phosphoryl azide (0.15 ml, 0.69 mmol) was added to a stirred solution of 3-carboxy-4-ethyl-9-isopropyl-9H-pyrido[3,4-b]indole (Method 3; 186 mg, 0.66 mmol) and triethylamine (0.1 ml, 0.69 mmol) in toluene (5 ml). The mixture was heated to 80° C. for 2 hours. 2-Trimethylsilylethanol (0.19 ml, 1.32 mmol) was then added and the mixture was allowed to stir for a further 6 hours at 80° C. The mixture was concentrated in vacuo and the residue was dissolved in EtOAc, washed with 1M NaOH and then with water. The organic phase was separated, dried and evaporated in vacuo. The crude product was purified by flash chromatography eluting over a gradient of 0-5% MeOH in DCM. The product was obtained as a light brown oil (84 mg) after evaporation of the appropriate fractions. NMR (300 MHz, CDCl3) 8.70 (s, 1H), 8.16 (d, 1H), 7.54 (m, 2H), 7.21 (m, 1H), 6.66 (s, 1H), 4.98 (m, 1H), 4.22 (m, 2H), 3.25 (q, 2H), 1.69 (d, 6H), 1.38 (t, 3H), 1.01 (m, 2H).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with 1M NaOH
  4. customThe organic phase was separated
  5. customdried
  6. customevaporated in vacuo
  7. customThe crude product was purified by flash chromatography
  8. washeluting over a gradient of 0-5% MeOH in DCM

Quellen und Nachweise

ORD-Eintrag
ord-66668697d8d242f885c7b1877a463bb1
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07408064B2

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