Potassium Carbonate → {2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid

HRID 1807632Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807632
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:29][C:30]([O:32]CCCC)=[O:31].C(=O)([O-])[O-].[K+].[K+]>>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH3:20])[C:8]=2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[O:27][CH2:29][C:30]([OH:32])=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 3

HCID 11430Potassium CarbonateHCID 87883Butyl bromoacetateHCID 58317807methyl 3-cyclohexyl-2-(2-hydroxyphenyl)-1-methyl-1H-indole-6-carboxylate

Produkt 1

HCID 58317804{2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acidAusbeute 90,6 %

Versuchsvorschrift

A solution of intermediate 4 (4.00 g, 11.0 mmol), tent-butyl 2-bromoacetate (2.36 g, 12.1 mmol) and potassium carbonate (3.04 g, 22.0 mmol) was stirred at room temperature. After 72 h, the reaction mixture was concentrated under vacuum and the residue was partitioned between CH2Cl2 and water. The organic layer was dried and the residue was reconstituted in CH2Cl2 (20 mL) and TFA (20 mL) was added. After 2 h at room temperature, the reaction mixture was evaporated under vacuum to yield 4.2 g (90%) of {2-[3-cyclohexyl-6-(methoxycarbonyl)-1-methyl-1H-indol-2-yl]phenoxy}acetic acid 5: m/z=422 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated under vacuum
  2. customthe residue was partitioned between CH2Cl2 and water
  3. customThe organic layer was dried
  4. additionTFA (20 mL) was added
  5. waitAfter 2 h at room temperature
  6. customthe reaction mixture was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-03270805739849bea63906bf04f32bb0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357687B2

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