Sodium Hydroxide → HCID 178504690, compound

HRID 710087Notes

Reaction equation

HRID 710087 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[F:10][C:11]1[CH:19]=[C:18]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[CH:16][C:12]=1[C:13](O)=O.[OH-].[Na+]>CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:13]([C:12]3[CH:16]=[CH:17][C:18]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:19][C:11]=3[F:10])=[N:9][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3235934-Bromobenzene-1,2-diamineHCID 283559322-Fluoro-4-(methylsulphonyl)benzoic acid

Product 1

HCID 178504690HCID 178504690, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
195 °C

Procedure

4-bromobenzene-1,2-diamine (1.75 g, 9.39 mmol) and 2-fluoro-4-(methylsulfonyl)benzoic acid (2 g, 9.39 mmol) were dissolved in polyphosphoric acid (70 g). This mixture was heated at 195° C. for three and half hours. Reaction mixture cooled to rt and diluted with ice water (100 ml). Aqueous layer basified with sodium hydroxide pellets to pH 9. Work up (EtOAc/H2O) followed by removal of EtOAc afforded the crude. Crude was purified on combiflash with a gradient mixture of EtOAc and Petether (33:67) to obtain the titled compound (1.5 g) as an off-white solid.

Workup

  1. customReaction mixture
  2. temperaturecooled to rt
  3. customfollowed by removal of EtOAc
  4. customafforded the crude
  5. customCrude was purified on combiflash with a gradient mixture of EtOAc and Petether (33:67)

Sources & evidence

ORD record
ord-4c4a6b4001af425f9afd79f155b7eb72
Source dataset
uspto-grants-2015_11
Patent number
US09181214B2

Reaction notes

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