N-bromobutanimide → Ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoate

HRID 537062Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][CH:14]=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=2)[C:8]([CH3:21])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>CN(C=O)C>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:29])=[C:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:12]=2)[C:8]([CH3:21])=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-3-furoate (20.0 g, 69.9 mmol) in DMF (90 mL) was added NBS (29.6 g, 168.1 mmol). The reaction mixture was allowed to stir at 80° C. overnight and then concentrated. The residue was washed with EtOH and filtered to give ethyl 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furoate (20 g, 60%).

Workup

concentrationconcentrated
washThe residue was washed with EtOH
filtrationfiltered

Sources & evidence

ORD record: ord-7f6fd8cc03f944ee8a3915adc15f1eda
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859768B2

Reaction notes

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