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Sodium hydride → 3-Cyclohexyl-1-dimethylcarbamoylmethyl-2-phenyl-1H-indole-6-carboxylic acid

HRID 1713925
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1713925
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34]>CN(C=O)C.CCOC(C)=O>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([OH:18])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:32][C:33]([N:35]([CH3:37])[CH3:36])=[O:34])[C:8]=2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1
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Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 68436344tert-butyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate

Produkt 1

HCID 52754443-Cyclohexyl-1-dimethylcarbamoylmethyl-2-phenyl-1H-indole-6-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

Tert-Butyl 3-cyclohexyl-2-phenyl-1H-indole-6-carboxylate (from Step 5) was dissolved in DMF (0.18 M). NaH (60% suspension in mineral oil, 1.5 eq.) was added and the resultant mixture stirred for 5 min at RT, then for another 5 min at 50° C. The solution was allowed to reach RT, and then neat 2-chloro-N,N-dimethylacetamide (1.6 eq.) was added dropwise. After 1 h analytical RP HPLC indicated complete conversion of the starting material. The mixture was diluted with EtOAc, and then washed with water (3×) and brine. Drying over Na2SO4 and evaporation gave a colorless solid, which was purified by flash chromatography on silica gel using PE/EtOAc (3:1, then 2:1) as the eluent. The resulting colorless solid was immediately dissolved in a mixture of DCM and TFA (0.05 M, 1:1, v/v). After stirring for 30 min at RT, the solvents were removed in vacuo to give after drying under high-vacuum, the title compound as a light yellow foam. 1H NMR (400 MHz, DMSO-d6, 300 K) δ 1.12-1.31 (m, 3H), 1.60-1.75 (m, 5H), 1.80-1.92 (m, 2H), 2.53-2.59 (m, 1H), 2.80 (s, 3H), 2.89 (s, 3H), 4.84 (s, 2H), 7.31 (d, J 6.4, 2H), 7.48-7.53 (m, 3H), 7.64 (d, J 8.4, 1H), 7.81 (d, J 8.4, 1H), 7.92 (s, 1H,); MS (ES+) m/z 405 (M+H)+

Aufarbeitung

  1. customto reach RT
  2. waitAfter 1 h analytical RP HPLC indicated complete
  3. washwashed with water (3×) and brine
  4. dry with materialDrying over Na2SO4 and evaporation
  5. customgave a colorless solid, which
  6. customwas purified by flash chromatography on silica gel using PE/EtOAc (3:1
  7. dissolutionThe resulting colorless solid was immediately dissolved in a mixture of DCM and TFA (0.05 M, 1:1
  8. customthe solvents were removed in vacuo
  9. customto give
  10. customafter drying under high-vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2b89aaf707f94ae6a7be4461d387ac57
Quelldatensatz
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07795250B2

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