3-Amino-5-bromopyridine → HCID 68228815, compound

HRID 1182944Notes

Reaction equation

HRID 1182944 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[C:12]([Cl:20])[CH:11]=1>N1C=CC=CC=1>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)(=[O:17])=[O:18])=[C:12]([Cl:20])[CH:11]=1

Participants

4

Reactant 2

HCID 8176813-Amino-5-bromopyridineHCID 27347664-Bromo-2-chlorobenzenesulfonyl chloride

Product 1

HCID 68228815HCID 68228815, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 5-bromopyridin-3-amine (0.300 g, 1.73 mmol) in pyridine (8.67 ml) was slowly added 4-bromo-2-chlorobenzene-1-sulfonyl chloride (0.600 g, 2.08 mmol) at 0° C. The reaction mixture was stirred for 2 hours at room temperature. The reaction mixture was quenched with 1 N aq. HCl, and then extracted with DCM (2×50 mL). The combined organic layers were washed brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting residue was recrystallized from EtOAc-hexanes to give 4-bromo-N-(5-bromopyridin-3-yl)-2-chlorobenzenesulfonamide (0.530 g, 72%) as a red solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.53-7.55 (1H, m), 7.71 (1H, d, J=1.6 Hz), 7.78 (1H, t, J=2.2 Hz), 7.89 (1H, d, J=8.4 Hz), 8.26 (1H, d, J=2.0 Hz). 8.44 (1H, d, J=2.4 Hz).

Workup

  1. customat 0° C
  2. customThe reaction mixture was quenched with 1 N aq. HCl
  3. extractionextracted with DCM (2×50 mL)
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was recrystallized from EtOAc-hexanes

Sources & evidence

ORD record
ord-946ebaac0c334c188a3e2a7d5279be99
Source dataset
uspto-grants-2014_03
Patent number
US08664230B2

Reaction notes

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