Methyl iodide → HCID 66793909, compound

HRID 1623514Notes

Reaction equation

HRID 1623514 reaction equation
[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([Br:12])[CH:11]=1)(=[O:5])=[O:4].[CH:14]([N-]C(C)C)(C)C.[Li+].IC>C1COCC1>[CH3:1][N:2]([CH3:13])[S:3]([C:6]1[CH:7]=[N:8][CH:9]=[C:10]([Br:12])[C:11]=1[CH3:14])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 467389545-Bromo-N,N-dimethylpyridine-3-sulfonamide

Product 1

HCID 66793909HCID 66793909, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-pyridine-3-sulfonic acid dimethylamide (CAS #896160-99-9, 100 mg, 0.377 mmol) in THF (3.8 mL) at −78° C. was added lithium diisopropylamide (0.5 M solution in THF, 0.85 mL, 0.42 mmol). The reaction was stirred for 15 minutes, at which time iodomethane (0.030 mL, 0.48 mmol) was added. The reaction was stirred for an additional 15 minutes and was then quenched with saturated aqueous ammonium chloride. Next, the reaction was diluted with water, dichloromethane, and saturated aqueous sodium bicarbonate. The layers were separated and aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/0.1% NH4OH) to furnish 5-bromo-4-methyl-pyridine-3-sulfonic acid dimethylamide; MS: (ES+) m/z 279.0 (M+H)+.

Workup

  1. additionwas added
  2. customwas then quenched with saturated aqueous ammonium chloride
  3. additionNext, the reaction was diluted with water, dichloromethane, and saturated aqueous sodium bicarbonate
  4. customThe layers were separated
  5. extractionaqueous layer was extracted two additional times with dichloromethane
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by semi-preparative reverse phase HPLC (20 to 90% acetonitrile/water w/0.1% NH4OH)

Sources & evidence

ORD record
ord-ad7d9ca686dd42359538410ce3c26b6b
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

Loading…