Cesium carbonate → 1-((1H-indol-4-yl)methyl)-9-(quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-one

HRID 41553Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41553
C([O-])([O-])=O.[Cs+].[Cs+].[N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N:17]1[CH2:48][CH2:47][C:20]2([N:25]([CH2:26][C:27]3[CH:35]=[CH:34][CH:33]=[C:32]4[C:28]=3[CH:29]=[CH:30][N:31]4S(C3C=CC(C)=CC=3)(=O)=O)[C:24](=[O:46])[CH2:23][CH2:22][CH2:21]2)[CH2:19][CH2:18]1>CO>[NH:31]1[C:32]2[C:28](=[C:27]([CH2:26][N:25]3[C:20]4([CH2:19][CH2:18][N:17]([C:8]5[CH:9]=[N:10][C:11]6[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=6)[N:7]=5)[CH2:48][CH2:47]4)[CH2:21][CH2:22][CH2:23][C:24]3=[O:46])[CH:35]=[CH:34][CH:33]=2)[CH:29]=[CH:30]1

Komponenten

4

Edukt 2

HCID 10796Cesium carbonateHCID 672524679-(quinoxalin-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one

Produkt 1

HCID 672523781-((1H-indol-4-yl)methyl)-9-(quinoxalin-2-yl)-1,9-diazaspiro[5.5]undecan-2-oneAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Cs2CO3 (0.201 g, 0.621 mmol) was added to a stirred solution of 9-(quinoxalin-2-yl)-1-((1-tosyl-1H-indol-4-yl)methyl)-1,9-diazaspiro[5.5]undecan-2-one (0.12 g, 0.207 mmol) in methanol (8.0 mL) and stirring was continued for 16 h at 80° C. under a nitrogen atmosphere. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (2×125 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by preparative HPLC under neutral conditions to yield the title compound as a yellow solid (0.022 g, 25%). [1H-NMR (CDCl3, 300 MHz): δ 8.5 (s, 1H), 8.21 (brs, 1H), 7.88 (d, 1H), 7.91-7.55 (m, 2H), 7.42 (t, 1H), 7.19-7.08 (m, 2H), 6.85 (d, 1H), 6.49-6.42 (m, 1H), 4.99 (s, 2H), 4.49-4.36 (m, 2H), 3.12 (t, 2H), 2.69 (t, 2H), 2.25-2.10 (m, 4H), 2.03-1.90 (m, 2H), 1.78 (d, 2H); HPLC RtA=4.393 min (98%); LCMS RtE=1.753, [M+H]+=426.1].

Aufarbeitung

  1. customThe reaction mixture was quenched with ice-cold water
  2. extractionextracted with ethyl acetate (2×125 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC under neutral conditions

Quellen und Nachweise

ORD-Eintrag
ord-17de531ae7d543318d0b7821bee1165c
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530648B2

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