N-Bromosuccinamide → N-(5'-Bromo-6-fluoro-3,4'-bipyridin-2'-yl)-N'-ethylurea

HRID 2243058Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([C:13]2[CH:14]=[N:15][C:16]([F:19])=[CH:17][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][C:16]([F:19])=[CH:17][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′-(6-fluoro-3,4′-bipyridin-2′-yl)urea (Intermediate 32, 360 mg, 1.38 mmol) in DMF (7 mL), N-bromosuccinamide (246 mg, 1.38 mmol) was added. The resulting solution was heated to 80° C. and stirred at that temperature for 2 hours. Then the reaction was partitioned between water and ethyl acetate. The layers separated, and the organic layer was washed with 5% sodium thiosulfate solution, water and brine, then dried over magnesium sulfate and concentrated. The solid obtained was washed with acetonitrile and dried to give the title compound as an off-white solid (390 mg). MS (ESP): 340 (M+1) for C13H12FN4O; NMR: 1.07 (t, 3H); 3.12-3.18 (m, 2H); 7.36-7.40 (m, 2H); 7.68 (s, 1H); 8.15 (t, 1H); 8.34 (d, 1H); 8.47 (s, 1H); 9.36 (s, 1H).

Workup

customThen the reaction was partitioned between water and ethyl acetate
customThe layers separated
washthe organic layer was washed with 5% sodium thiosulfate solution, water and brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customThe solid obtained
washwas washed with acetonitrile
customdried

Sources & evidence

ORD record: ord-491403fb9c8f47eaa02ccd6c6336cd29
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674801B2

Reaction notes

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