Sodium hydride → 5-(2-Morpholin-4-yl-ethoxy)-1H-pyrrolo[2,3-b]pyridine

HRID 2261588Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[C:13]1[CH:14]=[C:15]2[C:19](=[N:20][CH:21]=1)[NH:18][CH:17]=[CH:16]2>CN(C)C=O.[Cu]Br>[N:1]1([CH2:7][CH2:8][O:9][C:13]2[CH:14]=[C:15]3[CH:16]=[CH:17][NH:18][C:19]3=[N:20][CH:21]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

To 4-morpholineethanol (30 mL, 0.2 mol) in N,N-dimethylformamide (30 mL) was slowly added sodium hydride (7 g, 60% dispersion in mineral oil, 0.2 mol). After the solution turned clear, a solution of 5-bromo-7-azaindole (44, 1.0 g, 0.0051 mol) in N,N-dimethylformamide (5 mL) and copper(I) bromide (1.4 g, 0.0098 mol) were added. The reaction mixture was stirred at 120° C. under nitrogen for 2 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate and water. The organic layer was collected, washed with a solution of ammonium chloride and ammonium hydroxide (4:1), brine, and dried over magnesium sulfate. After removal of solvent, the residue was purified by silica gel column chromatography eluting with ethyl acetate in hexane to provide the compound as an off-white solid (79, 0.62 g, 50%). MS (ESI) [M+H+]+=248.25.

Workup

concentrationThe reaction mixture was concentrated
dissolutionthe residue was dissolved in ethyl acetate
customThe organic layer was collected
washwashed with a solution of ammonium chloride and ammonium hydroxide (4:1), brine
dry with materialdried over magnesium sulfate
customAfter removal of solvent
customthe residue was purified by silica gel column chromatography
washeluting with ethyl acetate in hexane

Sources & evidence

ORD record: ord-59334c136b954145bf6b6e3dbbe179f1
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846941B2

Reaction notes

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