Sodium hydride → Ethyl3-Formyl-2-isopropyl-1-(pyridin-3-ylmethyl)-1H-indole-6-carboxylate

HRID 40063

Reaktionsgleichung

[CH2:1]([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([CH:18]=[O:19])=[C:11]([CH:15]([CH3:17])[CH3:16])[NH:12]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[H-].[Na+].Br[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>CN(C=O)C.CCOC(C)=O>[CH:18]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=2)[N:12]([CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[C:11]=1[CH:15]([CH3:16])[CH3:17])=[O:19]

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

To a solution of ethyl3-formyl-2-isopropyl-1H-indole-6-carboxylate (Compound 34, 1.00 g, 3.86 mmol) in DMF (50 ml) was added NaH (463 mg, 19.3 mmol) and and 3-(bromomethyl)pyridine (2.62 g, 15.4 mmol). The reaction was stirred at 60° C. for 12 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→70% EtOAc-hexanes) to yield the title compound as a light yellow solid.

Aufarbeitung

washwashed with H2O, brine
dry with materialdried over Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by chromatography on silica gel (0→70% EtOAc-hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-4f088dfd9b5541b2a7a9d0b36e5f6f3a
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08524917B2

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