4-Methoxybenzenesulfonyl chloride → HCID 51355175, compound

HRID 1052473Notes

Reaction equation

HRID 1052473 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1.C(=O)(O)[O-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][S:28]([C:25]2[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[CH:27][CH:26]=2)(=[O:30])=[O:29])[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 51355175HCID 51355175, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-2-chloropyridin-3-amine (1 g, 4.82 mmol) was dissolved in THF (5.5 ml) and a solution of sodium bis(trimethylsilyl)amide (1M in THF, 14.5 ml, 14.5 mmol) was added dropwise. Ten minutes later, 4-methoxybenzene-1-sulfonyl chloride (3 g, 14.5 mmol) was added and the reaction mixture stirred for 2 h. A saturated solution of sodium bicarbonate was then added dropwise and the reaction mixture extracted with dichloromethane (×3). The organic phase was dried over magnesium sulphate, filtered and the solvent evaporated under reduced pressure. The resulting crude was purified by flash chromatography using SP1® Purification System (0% to 10%, dichloromethane-ethyl acetate) to obtain 1.49 g (82% yield) of the title compound. Purity: 100%

Workup

  1. extractionthe reaction mixture extracted with dichloromethane (×3)
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated under reduced pressure
  5. customThe resulting crude was purified by flash chromatography
  6. customSP1® Purification System (0% to 10%, dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-26c148f96d4e476a8789d446470d163f
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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