Dichloromethane → HCID 89784426, compound

HRID 1055984Notes

Reaction equation

HRID 1055984 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9](Cl)[CH:8]=[N:7]2.[C:13]([NH2:17])([CH3:16])([CH3:15])[CH3:14].C(Cl)Cl>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:17][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[N:7]2

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6385Tert-ButylamineHCID 593926708-Bromo-2-chloroquinoxaline

Product 1

HCID 89784426HCID 89784426, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 8-bromo-2-chloroquinoxaline (Example 210e; 1.53 g, 6.28 mmol) and tert-butylamine (Aldrich; 3.30 mL, 31.4 mmol) in DMSO (15 mL) was stirred at 100° C. for 2 h. The mixture was treated with DCM (100 mL), and washed with saturated aq. NaHCO3 (2×50 mL) and brine (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated. The crude material was purified on a silica gel column (23-32% EtOAc in hexanes) affording 8-bromo-N-(tert-butyl)quinoxalin-2-amine (1.75 g, 97% yield) as a yellow viscous oil which crystallized upon standing. 1H NMR (400 MHz, CDCl3) δ ppm 8.05 (1H, s), 7.85 (1H, d, J=7.6 Hz), 7.78 (1H, d, J=7.8 Hz), 7.19 (1H, t, J=7.9 Hz), 4.89 (1H, br. s.), 1.61 (9H, s). m/z (ESI, +ve) 280/282 (M+H)+.

Workup

  1. washwashed with saturated aq. NaHCO3 (2×50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified on a silica gel column (23-32% EtOAc in hexanes)

Sources & evidence

ORD record
ord-982ba62166c24cbcadf9bf51bbeca976
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

Loading…