Pyridine → N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamide

HRID 1096791Notes

Reaction equation

HRID 1096791 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.N1C=CC=CC=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Cl)Cl>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:24])=[O:23])[C:3]([Cl:9])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 57843322N-(5-Bromo-2-chloropyridin-3-yl)benzenesulfonamideYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-amino-5-bromo-2-chloropyridine (5.0 g, 24 mMol) in CH2Cl2 (50 mL) was added pyridine (3.0 mL, 37 mMol) followed by benzenesulfonyl chloride (4.5 mL, 35 mMol) drop wise over 5 minutes. The reaction was stirred at RT for 18 h and evaporated to dryness under vacuum. Purified by flash chromatography on silica gel (15% hexanes in CH2Cl2 then 0 to 5% EtOAc in 15% hexanes in CH2Cl2). During evaporation of the solvents the product crashed out. The resultant slurry was diluted with hexane, filtered and dried under vacuum to give the title compound (2.89 g, 34%) as a white solid. [An overlap fraction which contained 30% starting amine (2.60 g) was also obtained.]: 1H NMR (400 MHz, DMSO-d6) δ ppm 10.61 (br. s., 1H), 8.41 (d, J=2.27 Hz, 1H), 7.91 (d, J=2.27 Hz, 1H), 7.73-7.77 (m, 2H), 7.67-7.72 (m, 1H), 7.56-7.64 (m, 2H); MS(ES) m/e 346.7 (M+H)+.

Workup

  1. customevaporated to dryness under vacuum
  2. customPurified by flash chromatography on silica gel (15% hexanes in CH2Cl2
  3. customDuring evaporation of the solvents the product
  4. additionThe resultant slurry was diluted with hexane
  5. filtrationfiltered
  6. customdried under vacuum

Sources & evidence

ORD record
ord-be33e996061f4968935f59cdf3a3d97d
Source dataset
uspto-grants-2012_03
Patent number
US08138347B2

Reaction notes

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