1-Bromo-2-methylpropane → 2-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamide

HRID 594101Notes

Reaction equation

HRID 594101 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N:14]=1)(=[O:11])=[O:10].[CH3:21][C:22](N=C(N(C)C)N(C)C)([CH3:24])[CH3:23].BrCC(C)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([N:12]([C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N:14]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])(=[O:10])=[O:11]

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 89876078HCID 89876078, compound

Product 1

HCID 898760522-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluoro-N-isobutylbenzenesulfonamideYield 6.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-N-(3,5-dimethylpyridin-2-yl)-4-fluorobenzenesulfonamide (117 mg, 0.372 mmol) in acetonitrile (4 mL) stirred at room temperature, was added N″-(1,1-dimethylethyl)-N,N,N′,N′-tetramethylguanidine (127 mg, 0.743 mmol). The reaction mixture was stirred at room temperature for 1 hour, then 1-bromo-2-methylpropane (0.081 mL, 0.743 mmol) was added. The reaction vessel was sealed and heated under microwaves at 150° C. for 30 minutes. The solvent was evaporated in vacuo and the crude was purified by mass directed autoprep (ammonium carbonate modifier) to give the title compound (8.4 mg). LCMS (2 min, High pH) Rt 1.45 min, m/z (ES+) 371 (M+H).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureheated under microwaves at 150° C. for 30 minutes
  3. customThe solvent was evaporated in vacuo
  4. customthe crude was purified by mass

Sources & evidence

ORD record
ord-cda3364511ab466e8b95b633ae361bfd
Source dataset
uspto-grants-2016_01
Patent number
US09242972B2

Reaction notes

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