Tert-Butylamine → 8-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine

HRID 1056065Notes

Reaction equation

HRID 1056065 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5](F)[C:6]([CH3:12])=[N:7]2.[C:14]([NH2:18])([CH3:17])([CH3:16])[CH3:15]>CS(C)=O.C(Cl)Cl>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[N:4]=[C:5]([NH:18][C:14]([CH3:17])([CH3:16])[CH3:15])[C:6]([CH3:12])=[N:7]2

Participants

5

Reactant 2

HCID 6385Tert-ButylamineHCID 897819405-Bromo-3-fluoro-2-methylquinoxaline

Product 1

HCID 897836188-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-3-fluoro-2-methylquinoxaline (Example 126f; 1.05 g, 4.36 mmol) and tert-butylamine (2.29 mL, 21.8 mmol) in DMSO (10 mL) was stirred at 100° C. for 2.5 h. The mixture was then diluted with DCM (150 mL) and washed with saturated aq. NaHCO3 (3×100 mL). The organic layer was separated, dried over MgSO4, filtered, and concentrated. The crude material was adsorbed onto silica and chromatographically purified (silica gel; 0-4% MeOH in DCM) to give 8-bromo-N-(tert-butyl)-3-methylquinoxalin-2-amine as an amorphous pink solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.82 (d, J=7.6 Hz, 1H), 7.68-7.74 (m, 1H), 7.22 (t, J=7.9 Hz, 1H), 6.17 (s, 1H), 2.55 (s, 3H), 1.58 (s, 9H). m/z (ESI, +ve ion) 294.0/296.0 (M+H)+.

Workup

  1. washwashed with saturated aq. NaHCO3 (3×100 mL)
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographically purified (silica gel; 0-4% MeOH in DCM)

Sources & evidence

ORD record
ord-58d0732c2b454b7bb307c02b8fbdbef0
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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