Pyridine → HCID 90102463, compound

HRID 1052643Notes

Reaction equation

HRID 1052643 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.N1C=CC=CC=1.[F:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=1[S:24](Cl)(=[O:26])=[O:25]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][S:24]([C:17]2[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=2[F:15])(=[O:25])=[O:26])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 8176813-Amino-5-bromopyridineHCID 201155242-Fluoro-4-Methoxybenzenesulfonyl Chloride

Product 1

HCID 90102463HCID 90102463, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Bromopyridin-3-amine (500 mg, 2.89 mmol) was dissolved in dichloromethane (14 ml) and pyridine (4 ml) was added. To this mixture 2-fluoro-4-methoxybenzene-1-sulfonyl chloride (1 g, 4.45 mmol) was added dropwise and the mixture stirred at reflux for 5 h. Once at room temperature, the reaction mixture was washed with water and brine, dried over magnesium sulphate, filtered and the solvents were removed under reduced pressure. The product was purified by flash chromatography (0% to 50% DCM/AcOEt) to give 792 mg (76% yield) of the title compound as a white solid.

Workup

  1. temperatureat reflux for 5 h
  2. washOnce at room temperature, the reaction mixture was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customThe product was purified by flash chromatography (0% to 50% DCM/AcOEt)

Sources & evidence

ORD record
ord-baeab1552b354bbfaad1c93aec94c810
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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