Potassium Hydroxide → HCID 57545848, compound

HRID 1485543Notes

Reaction equation

HRID 1485543 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:9](S(C2C=CC(F)=CC=2F)(=O)=O)[S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])(=[O:12])=[O:11])[C:5]([Cl:8])=[N:6][CH:7]=1.[OH-].[K+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])(=[O:11])=[O:12])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 88898431HCID 88898431, compound

Product 1

HCID 57545848HCID 57545848, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-(5-bromo-2-chloropyridin-3-yl)-N-(2,4-difluorophenylsulfonyl)-2,4-difluorobenzenesulfonamide (19.3 g, 34.4 mmol) in dioxane (340 ml) was heated at 80° C. And then 2 N aq. KOH (86.0 ml, 172 mmol) was added to the mixture. After stirring for 30 min, the reaction mixture was cooled to room temperature, and then quenched with 1 N aq. HCl until pH 3. The resulting solid was collected by filtration and washed with water to give the N-(5-bromo-2-chloropyridin-3-yl)-2,4-difluorobenzenesulfonamide (8.36 g, 63.4%) as a white solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 7.25 (1H, t, J=8.4 Hz), 7.58 (1H, t, J=9.2 Hz), 7.77-7.83 (1H, m), 8.03 (1H, d, J=2.0 Hz), 8.44 (1H, d, J=2.0 Hz), 11.04 (1H, brs).

Workup

  1. customquenched with 1 N aq. HCl until pH 3
  2. filtrationThe resulting solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-05e2579424c6430f822fb34b36b9a218
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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