Bromoacetyl bromide → HCID 46916455, compound

HRID 2045933Notes

Reaction equation

HRID 2045933 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[CH:3][C:2]=1[C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[CH:15][CH:16]=1.[Br:18][CH2:19][C:20](Br)=[O:21].C(N(C(C)C)CC)(C)C>C1COCC1.C(OCC)(=O)C>[Br:18][CH2:19][C:20]([NH:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:2]2[CH:3]=[N:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[N:1]=2)[CH:12]=1)=[O:21]

Participants

6

Reactant 3

HCID 61147Bromoacetyl bromideHCID 81531DiisopropylethylamineHCID 8072643-(2-quinoxalinyl)aniline

Product 1

HCID 46916455HCID 46916455, compoundYield 22.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3-quinoxalin-2-ylphenyl)amine (2 g, 9.04 mmol) in THF (50 mL), bromoacetyl bromide (0.83 mL, 9.5 mmol) was added, followed by diisopropylethylamine (DIEA, 1.8 mL, 10.85 mmol), at room temperature. The reaction mixture was stirred at room temperature for 24 hrs, the slurry was diluted with ethyl acetate and the organic phase was washed with water (50 mL). The insoluble solid was filtered and analysed to afford 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (700 mg, 22% yield). The mother liquer was evaporated in vacuo to afford a second batch of 2-bromo-N-(3-(quinoxalin-2-yl)phenyl)acetamide (1.8 g, 58% yield). LCMS calculated for C18H15N3O (M+H): 290.33. found 290.24. 1H-NMR (DMSO-d6, 400 Mhz) δH: 10.62 (1H, br.), 9.52 (1H, s), 8.55 (1H, m), 8.12-8.18 (2H, m), 8.05-8.08 (1H, m), 7.80-7.95 (3H, m), 7.55-7.60 (1H, m), 4.12 (2H, s).

Workup

  1. washthe organic phase was washed with water (50 mL)
  2. filtrationThe insoluble solid was filtered

Sources & evidence

ORD record
ord-463ad31e067a4c068767d7b3c58be48b
Source dataset
uspto-grants-2013_11
Patent number
US08592415B2

Reaction notes

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