Chloromethyl Methyl Ether → N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl-benzenesulfonamide

HRID 1480893Notes

Reaction equation

HRID 1480893 reaction equation
[Br:1][C:2]1[C:7]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:29][O:30][CH2:31]Cl>C1COCC1>[Br:1][C:2]1[C:7]([N:8]([CH2:29][O:30][CH3:31])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([CH3:19])([CH3:21])[CH3:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:22])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 57942597N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide

Product 1

HCID 57942088N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-N-methoxymethyl-benzenesulfonamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution N-(2-bromo-5-chloro-pyridin-3-yl)-4-tert-butyl-benzenesulfonamide (12.0 g, 35.0 mmol) and K2CO3 (24.0 g, 170 mmol) in 80 mL anhydrous THF was added chloromethyl methyl ether (4.0 mL, 52.7 mmol). The resultant heterogeneous solution was stirred for 60 minutes at ambient temperature and the solids were subsequently removed via filtration. The filtrate was then removed in vacuo and the residue was dissolved in EtOAc. The organics were washed with saturated Na2CO3, dried over MgSO4, and evaporated in vacuo to generate a brownish oil. The oil was finally triturated with hexanes and the resultant solid filtered to produce the desired product as a light yellowish solid (11.5 g, 86% yield): MS (ES) M+H expected 447.0, found 447.0.

Workup

  1. customthe solids were subsequently removed via filtration
  2. customThe filtrate was then removed in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washThe organics were washed with saturated Na2CO3
  5. dry with materialdried over MgSO4
  6. customevaporated in vacuo
  7. customThe oil was finally triturated with hexanes
  8. filtrationthe resultant solid filtered

Sources & evidence

ORD record
ord-fa7916150f174a67a1c1964e8f6a4bdb
Source dataset
uspto-grants-2016_08
Patent number
US09409909B2

Reaction notes

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