N-bromobutanimide → HCID 70654595, compound
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][CH:18]3[CH2:20][CH2:19]3)(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O>C(Cl)Cl>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([S:14]([NH:17][CH:18]3[CH2:20][CH2:19]3)(=[O:15])=[O:16])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[Br:21]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(6-amino-pyridin-3-yl)-N-cyclopropylbenzenesulfonamide (1.04 g, 3.59 mmol) in DCM (12 mL) was added portionwise N-bromosuccinimide (0.64 g, 3.59 mmol). The reaction was stirred for 1 h, then was filtered. The filtrate was washed with sat. aq. Na2S2O4 (20 mL), sat. aq. NaHCO3 (10 mL), then dried over Na2SO4 and concentrated to give 4-(6-amino-5-bromo-pyridin-3-yl)-N-cyclopropyl-benzenesulfonamide (1.07 g, 81% yield). 1H NMR (400 MHz, METHANOL-d4) δ ppm 8.30 (d, J=2.01 Hz, 1H), 8.12 (d, J=2.01 Hz, 1H), 7.92 (d, J=8.53 Hz, 2H), 7.76 (d, J=8.53 Hz, 2H), 2.19 (tt, J=6.71, 3.58 Hz, 1H), 0.17-0.83 (m, 4H). MS (EI) m/z: 368, 370 [M+H]+. HPLC (Sunfire C18 4.6 mm×50 mm, 10-90% MeCN:10 mM aq. NH4OAc, 2 min gradient) tR=1.68 min, 90% integrated area.