Water → (1-Bromo-imidazo[1,2-a]quinoxalin-4-yl)isobutyl-amine

HRID 1025481Notes

Reaction equation

HRID 1025481 reaction equation
[Br:1][C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14](Cl)[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.[CH2:16]([NH2:20])[CH:17]([CH3:19])[CH3:18].CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1>[Br:1][C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:20][CH2:16][CH:17]([CH3:19])[CH3:18])[C:5]2=[N:4][CH:3]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3

Participants

6

Reactant 4

HCID 962WaterHCID 6558IsobutylamineHCID 81531DiisopropylethylamineHCID 717416391-Bromo-4-chloroimidazo[1,2-A]quinoxaline

Product 1

HCID 66601580(1-Bromo-imidazo[1,2-a]quinoxalin-4-yl)isobutyl-amineYield 93.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a stirred solution of 1-bromo-4-chloro-imidazo[1,2-a]quinoxaline (14.13 g, 50 mmol) in NMP (400 mL) was added isobutylamine (9.94 mL, 100 mmol) and DIPEA (26.13 mL, 150 mmol) at room temperature in a microwave reactor. The solution was heated at 170° C. under microwave irradiation for 60 min. After cooling, water was added to the solution and the precipitate was filtered and the residue was washed with water and dried to give (1-bromo-imidazo[1,2-a]quinoxalin-4-yl)-isobutyl-amine (14.89 g, 93.3%): 1H-NMR (300 MHz, d6-DMSO): δ=9.17 (1H, d), 8.01 (1H, d), 7.92 (1H, s), 7.78 (1H, dd), 7.70 (1H, dd) ppm. UPLC-MS: RT=1.14 min; m/z 284.6 [MH+]; required MW=283.5.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered
  3. washthe residue was washed with water
  4. customdried

Sources & evidence

ORD record
ord-993f3a2439ee4c5ab1082183036ae4d3
Source dataset
uspto-grants-2014_05
Patent number
US08729082B2

Reaction notes

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