N-bromobutanimide → HCID 70654595, compound

HRID 2091583Notes

Reaction equation

HRID 2091583 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

HCID 67184N-bromobutanimideHCID 70654684HCID 70654684, compound

Product 1

HCID 70654595HCID 70654595, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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.

Workup

  1. filtrationwas filtered
  2. washThe filtrate was washed with sat. aq. Na2S2O4 (20 mL), sat. aq. NaHCO3 (10 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b19a074688984819955343522289d8da
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

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