4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide → N-(5-Bromo-2-chloro-3-pyridinyl)-4-(1-hydroxy-1-methylethyl)benzenesulfonamide

HRID 2077543Notes

Reaction equation

HRID 2077543 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[C:15]([Cl:21])=[N:16][CH:17]=[C:18]([Br:20])[CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH3:22][Mg]Br>C1COCC1>[Br:20][C:18]1[CH:19]=[C:14]([NH:13][S:10]([C:7]2[CH:8]=[CH:9][C:4]([C:1]([OH:3])([CH3:22])[CH3:2])=[CH:5][CH:6]=2)(=[O:12])=[O:11])[C:15]([Cl:21])=[N:16][CH:17]=1

Participants

4

Reactant 2

HCID 595195144-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamideHCID 178418573HCID 178418573, compound3×

Product 1

HCID 59519512N-(5-Bromo-2-chloro-3-pyridinyl)-4-(1-hydroxy-1-methylethyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide (123.5 mg, 0.317 mmol) was dissolved in THF (2.6 ml) and cooled in an ice water bath under nitrogen. Then, methylmagnesium bromide (0.65 ml, 1.4 M solution in toluene/tetrahydrofuran (75:25), 0.91 mmol) was added via syringe, and the reaction was allowed to slowly warm to room temperature. After 2 hours and 45 minutes, more methylmagnesium bromide (0.50 ml) was added, and stirring was continued at room temperature. After 75 minutes, more methylmagnesium bromide (0.93 ml) was added, and stirring was continued. After another hour, the reaction quenched with saturated ammonium chloride. The layers were separated, and the aqueous phase was extracted with 10:1 DCM/MeOH. Organic extracts combined, concentrated, and taken on to the next step. MS (ESI pos. ion) m/z: 405 (MH+, 79Br), 407 (MH+, 81Br). Calculated exact mass for C14H14BrClN2O3S 404 (79Br), 406 (81Br).

Workup

  1. temperaturecooled in an ice water bath under nitrogen
  2. customwas continued at room temperature
  3. waitAfter 75 minutes
  4. stirringstirring
  5. waitAfter another hour
  6. customthe reaction quenched with saturated ammonium chloride
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted with 10:1 DCM/MeOH
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-4ad14b7589fa4442a8991a7f70a95118
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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