N-bromobutanimide → HCID 178496268, compound

HRID 1843683Notes

Reaction equation

HRID 1843683 reaction equation
[F:1][C:2]1[C:7]([C:8]2[CH:12]=[CH:11][NH:10][N:9]=2)=[C:6]([F:13])[CH:5]=[CH:4][C:3]=1[N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[F:25])(=[O:17])=[O:16].[Br:32]N1C(=O)CCC1=O>C(Cl)Cl>[Br:32][C:12]1[C:8]([C:7]2[C:2]([F:1])=[C:3]([N:14]([CH2:26][O:27][CH2:28][CH2:29][O:30][CH3:31])[S:15]([C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[F:25])(=[O:17])=[O:16])[CH:4]=[CH:5][C:6]=2[F:13])=[N:9][NH:10][CH:11]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 178496267HCID 178496267, compound

Product 1

HCID 178496268HCID 178496268, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[2,4-difluoro-3-(1H-pyrazol-3-yl)-phenyl]-2,5-difluoro-N-(2-methoxyethoxy-methyl)-benzenesulfonamide (1.27 g, 2.76 mmol) was dissolved in dry DCM (10 mL). N-bromosuccinimide was then added (737 mg, 4.14 mmol, 1.5.eq) and the reaction was stirred at room temperature for 3 hours. The reaction mixture was then diluted with DCM and washed with 10% aqueous NaHSO3 and brine. The organic phase was dried over Na2SO4 and evaporated to dryness. The desired N-[3-(4-bromo-1H-pyrazol-3-yl)-2,4-difluoro-phenyl]-2,5-difluoro-N-(2-methoxyethoxymethyl)-benzenesulfonamide was isolated from the crude mixture by chromatography on silica gel (DCM/MeOH 95:5) obtaining 584 mg (39%) of off-white solid.

Workup

  1. washwashed with 10% aqueous NaHSO3 and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-4a8e16dbec2a4601a7b0c804747caafe
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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