Sodium Acetate → 2-Bromo-5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)benzyl acetate

HRID 1260176Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:4][C:3]=1[CH2:26]Br.[C:28]([O-:31])(=[O:30])[CH3:29].[Na+]>CN(C)C=O>[C:28]([O:31][CH2:26][C:3]1[CH:4]=[C:5]([N:8]([C:9]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:15])[C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([O:24][CH3:25])[N:17]=2)[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of tert-butyl 4-bromo-3-(bromomethyl)phenyl(5-cyano-6-methoxypyridin-2-yl)carbamate (4.46 g, 8.98 mmol) in N,N-dimethylformamide (60 mL) was added sodium acetate (3.68 g, 44.9 mmol). The reaction was stirred at 50° C. for two hours. The mixture was cooled to room temperature and extracted with ethyl acetate and water in portions. The organic layer of each portion was washed three times with water and brine, and dried over sodium sulfate, and filtered. The portions were combined and the solvent was removed under reduced pressure. The residue was purified by Combiflash to give 2-bromo-5-(tert-butoxycarbonyl(5-cyano-6-methoxypyridin-2-yl)amino)benzyl acetate (1.99 g, 2 steps 46%).

Workup

temperatureThe mixture was cooled to room temperature
extractionextracted with ethyl acetate and water in portions
washThe organic layer of each portion was washed three times with water and brine
dry with materialdried over sodium sulfate
filtrationfiltered
customthe solvent was removed under reduced pressure
customThe residue was purified by Combiflash

Sources & evidence

ORD record: ord-e70c0b02272947d59d491363562aa4f7
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470803B2

Reaction notes

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