N-Bromosuccinamide → N-(5'-bromo-5-fluoro-3,4'-bipyridin-2'-yl)-N'-ethylurea

HRID 2243057Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of N-ethyl-N′-(5-fluoro-3,4′-bipyridin-2′-yl)urea (Intermediate 29, 386 mg, 1.48 mmol) in DMF (7 mL), N-bromosuccinamide (396 mg, 2.22 mmol) was added. The resulting solution was heated to 80° C. and stirred at that temperature for 8 hours. The reaction mixture was partitioned between water and ethyl acetate. The layers were separated and the organic layer was washed with 5% sodium thiosulfate solution, water and brine. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The resulting solid was washed with acetonitrile and dried to give the title compound as an off-white solid (340 mg). MS (ESP): 340 (M+H+) for C13H12BrFN4O; NMR: 1.06 (t, 3H), 3.14 (q, 2H), 7.35 (t, 1H), 7.69 (s, 1H), 7.91-7.97 (m, 1H), 8.48 (s, 1H), 8.51 (t, 1H), 8.71 (d, 1H), 9.37 (s, 1H).

Workup

customThe reaction mixture was partitioned between water and ethyl acetate
customThe layers were separated
washthe organic layer was washed with 5% sodium thiosulfate solution, water and brine
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
washThe resulting solid was washed with acetonitrile
customdried

Sources & evidence

ORD record: ord-39270512dd7c43f6a7720ca219ecc672
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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