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

HRID 1099683Notes

Reaction equation

HRID 1099683 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][S:12]([C:15]1[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:19][CH:20]=1)(=[NH:14])=[O:13].Cl.CN(C)CCCN=C=NCC.CCOC(C)=O>CN(C1C=CN=CC=1)C.CN(C=O)C>[Br:1][C:2]1[CH:10]=[C:6]([C:7]([N:14]=[S:12]([C:15]2[CH:16]=[C:17]([CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:18]=[CH:19][CH:20]=2)([CH3:11])=[O:13])=[O:9])[CH:5]=[N:4][CH:3]=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-bfdfcdfcad5d4f79bcdb9a7d20df0a01
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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