Ethyl Acetate → 8-bromo-6-methyl-4,6-dihydro-2H-pyrido[4,3-b][1,4]oxazine-3,5-dione

HRID 575798Notes

Reaction equation

HRID 575798 reaction equation
[CH3:1][N:2]1[CH:12]=[CH:11][C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[C:3]1=[O:13].C1C(=O)N([Br:21])C(=O)C1.CC(=O)OCC>CC#N>[Br:21][C:11]1[C:5]2[O:6][CH2:7][C:8](=[O:10])[NH:9][C:4]=2[C:3](=[O:13])[N:2]([CH3:1])[CH:12]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimide2×HCID 1180216156-methyl-4H-pyrido[4,3-b][1,4]oxazine-3,5-dione

Product 1

HCID 1180214318-bromo-6-methyl-4,6-dihydro-2H-pyrido[4,3-b][1,4]oxazine-3,5-dioneYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

At room temperature, to the title compound of step 1 (90 mg, 0.5 mmol) in anhydrous CH3CN (1 mL) was added NBS (89 mg, 0.5 mmol). After stirring about 2 h, additional NBS (75 mg, 0.4 mmol) was added and the reaction was complete within 20 min. EA extractive work up and silica gel chromatography gave the title compound (51 mg, 0.39 mmol) in 39% yield.

Workup

  1. waitthe reaction was complete within 20 min

Sources & evidence

ORD record
ord-670a22c1db314c4e9e2b99f4b206593f
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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