Ethyl Acetate → Methyl (3-{N-[(5-bromopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}phenyl)acetate

HRID 607436Notes

Reaction equation

HRID 607436 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:11][O:12][C:13](=[O:25])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[NH:23])=[O:22])[CH:16]=1.Cl.CN(C)CCCN=C=NCC.CCOC(C)=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:11][O:12][C:13](=[O:25])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21]([CH3:24])(=[N:23][C:7]([C:6]2[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:10]=2)=[O:9])=[O:22])[CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57657973methyl [3-(S-methylsulfonimidoyl)phenyl]acetate

Product 1

HCID 57657931Methyl (3-{N-[(5-bromopyridin-3-yl)carbonyl]-S-methylsulfonimidoyl}phenyl)acetateYield 75.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-bromonicotinic acid (648 mg, 3.21 mmol), methyl[3-(S-methylsulfonimidoyl)phenyl]acetate (802 mg, 3.53 mmol), and catalytic DMAP in 15.0 ml DMF at room temperature was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (738 mg, 3.85 mmol). The reaction was stirred 1 hour at room temperature then added to EtOAc. The EtOAc solution was washed with dilute brine, NaHCO3 solution, brine, dilute HCl/brine mixture, brine/NaHCO3 solution, dried with anhydrous Na2SO4 and rotary evaporated. The oil was chromatographed eluting with CHCl3/EtOAc to give viscous clear oil (994 mg, 75%).

Workup

  1. washThe EtOAc solution was washed with dilute brine, NaHCO3 solution, brine, dilute HCl/brine mixture, brine/NaHCO3 solution
  2. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  3. customThe oil was chromatographed
  4. washeluting with CHCl3/EtOAc

Sources & evidence

ORD record
ord-ad965d48756a42b2a9946810242f3fb0
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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