Pyridine → HCID 21961420, compound

HRID 887663Notes

Reaction equation

HRID 887663 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:14][CH2:15][CH2:16][NH2:17])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].N1C=CC=CC=1.[S:24](Cl)([CH3:27])(=[O:26])=[O:25]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([O:14][CH2:15][CH2:16][NH:17][S:24]([CH3:27])(=[O:26])=[O:25])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 21961460HCID 21961460, compound

Product 1

HCID 21961420HCID 21961420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-((3-Nitro-5-(trifluoromethyl)phenyl)oxy)ethylamine (4.05 g, 16.2 mmols, 1 eq) was dissolved in 100 mL of CH2Cl2. The solution was cooled to 0° C. Pyridine (2.6 mL, 32.4 mmols, 2 eq) was added followed by mesyl chloride (1.25 mL, 16.2 mmols, 1 eq). The reaction was stirred for 18 h during which time it was warmed slowly to RT. The solvent was removed in vacuo, and the residue dissolved in EtOAc. The resulting solution was washed twice with 2 N HCl, once with water, and 3× with brine. After being dried over Na2SO4 the solution was filtered and concentrated. The crude was purified by silica gel chromatography eluting with 50% to 60% EtOAc:hexane to yield the desired compound.

Workup

  1. temperaturewas warmed slowly to RT
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in EtOAc
  4. washThe resulting solution was washed twice with 2 N HCl, once with water, and 3× with brine
  5. dry with materialAfter being dried over Na2SO4 the solution
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crude was purified by silica gel chromatography
  9. washeluting with 50% to 60% EtOAc

Sources & evidence

ORD record
ord-e12aecfffa584b18996b38598b5ab760
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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