2-Methylpyridine → 3-{1-(1,3-Benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-6-[2-(2-pyridyl)acetyl]-1H-indole

HRID 381341Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 381341
O1CCCC1.C([N-]C(C)C)(C)C.[Li+].[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1.CON(C)[C:24]([C:26]1[CH:34]=[C:33]2[C:29]([C:30]([CH:36]([C:50]3[CH:58]=[CH:57][C:53]4[O:54][CH2:55][O:56][C:52]=4[CH:51]=3)[C:37]([NH:39][S:40]([C:43]3[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=3)(=[O:42])=[O:41])=[O:38])=[CH:31][N:32]2[CH3:35])=[CH:28][CH:27]=1)=[O:25]>O1CCCC1>[O:54]1[C:53]2[CH:57]=[CH:58][C:50]([CH:36]([C:30]3[C:29]4[C:33](=[CH:34][C:26]([C:24](=[O:25])[CH2:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=5)=[CH:27][CH:28]=4)[N:32]([CH3:35])[CH:31]=3)[C:37]([NH:39][S:40]([C:43]3[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=3)(=[O:42])=[O:41])=[O:38])=[CH:51][C:52]=2[O:56][CH2:55]1

Komponenten

5

Edukt 3

HCID 79752-MethylpyridineHCID 10997623Lithium diisopropylamide mono(tetrahydrofuran)HCID 22467206N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide

Produkt 1

HCID 224672333-{1-(1,3-Benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1-methyl-6-[2-(2-pyridyl)acetyl]-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Lithium diisopropylamide mono(tetrahydrofuran) (0.53 ml of 1.5M solution in cyclohexane) was added to a stirred solution of 2-methylpyridine (0.08 ml, 0.8 mmol) in anhydrous tetrahydrofuran (3 ml) at −70° C. under a nitrogen atmosphere. After 20 minutes a solution of N6-methoxy-N6,1-dimethyl-3-{1-(1,3-benzodioxol-5-yl)-2-[(4-methylphenyl)sulfonamido]-2-oxoethyl}-1H-6-indolecarboxamide (the compound of Example 103, 200 mg, 0.36 mmol) in anhydrous tetrahydrofuran (2 ml) was added to the mixture at −70° C. The mixture was stirred at −70° C. for an additional 2 hours before being warmed to be 0° C. and then quenched with the addition of water (5 ml). The mixture was acidified with acetic acid, and extracted with ethyl acetate (100 ml). The organic phase was separated and washed with brine, dried (magnesium sulphate) and the solvent was removed in vacuo. The residue was flash chromatographed using a gradient elution of a mixture of 90% hexane and 10% ethyl acetate, through to 100% ethyl acetate, to give the title compound (95 mg).

Aufarbeitung

  1. temperaturebefore being warmed
  2. customto be 0° C.
  3. customquenched with the addition of water (5 ml)
  4. extractionextracted with ethyl acetate (100 ml)
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried (magnesium sulphate)
  8. customthe solvent was removed in vacuo
  9. customchromatographed
  10. washa gradient elution of a mixture of 90% hexane and 10% ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-da05712c13d642c3997c2123d1d56c82
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306852B1

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