Water → 5-Bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde

HRID 1056167Notes

Reaction equation

HRID 1056167 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([CH3:17])=[N:7]2.[Se](=O)=[O:19].O>O1CCOCC1.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:8]([CH:17]=[O:19])=[N:7]2

Participants

6

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 897836188-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine

Product 1

HCID 897823205-Bromo-3-(tert-butylamino)quinoxaline-2-carbaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 8-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine (174a) (137 mg, 0.47 mmol), selenium dioxide (Aldrich; 57.0 mg, 0.51 mmol), and water (0.084 mL, 4.67 mmol) in 1,4-dioxane (5.0 mL) was stirred under argon at 60° C. for 19 h. The reaction mixture was then cooled to RT, diluted with DCM (5 mL), and adsorbed onto silica gel. Chromatographic purification (silica gel, 0-10% EtOAc/hexanes) furnished 5-bromo-3-(tert-butylamino)quinoxaline-2-carbaldehyde (132. mg, 0.43 mmol, 92% yield) as a yellow-orange solid. 1H NMR (400 MHz, CDCl3) δ ppm 10.14 (1H, s), 8.03 (1H, br. s.), 7.99 (1H, d, J=7.4 Hz), 7.88 (1H, d, J=8.4 Hz), 7.22-7.25 (1H, m), 1.64 (9H, s). m/z (ESI, +ve) 308.0/310.1 (M+H)+.

Workup

  1. customChromatographic purification (silica gel, 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d30465d42bb24b9785a1bb773bedb9df
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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