o-Iodonitrobenzene → 4-chloro-N-{5-chloro-2-[hydroxy-(2-nitro-phenyl)-methyl]-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 1898093Notes

Reaction equation

HRID 1898093 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C1([Mg]Cl)C=CC=CC=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([C:33]2[C:34]([CH:40]=[O:41])=[N:35][CH:36]=[C:37]([Cl:39])[CH:38]=2)[CH2:30][O:31][CH3:32])(=[O:28])=[O:27])=[CH:22][C:21]=1[C:42]([F:45])([F:44])[F:43]>C1COCC1>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([C:33]2[C:34]([CH:40]([OH:41])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[N+:8]([O-:10])=[O:9])=[N:35][CH:36]=[C:37]([Cl:39])[CH:38]=2)[CH2:30][O:31][CH3:32])(=[O:28])=[O:27])=[CH:22][C:21]=1[C:42]([F:43])([F:45])[F:44]

Participants

5

Reactant 3

HCID 69115o-IodonitrobenzeneHCID 579420984-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamideHCID 178478979HCID 178478979, compound

Product 1

HCID 579421384-chloro-N-{5-chloro-2-[hydroxy-(2-nitro-phenyl)-methyl]-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-iodo-2-nitro-benzene (769 mg, 3.08 mmol) in anhydrous THF (3 mL) was added 2 M phenylmagnesiumchloride in THF (1.62 mL, 3.24 mmol) at −40° C. under an atmosphere of nitrogen. It was stirred at the same temperature for 15 minutes and then 4-chloro-N-(5-chloro-2-formyl-pyridin-3-yl)-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (1.04 g, 2.36 mmol) was added in one portion and the progress of the reaction was followed by LCMS. The reaction mixture was warmed to room temperature and stirred for 3 h. It was then quenched with saturated aqueous NH4Cl (2 mL), and extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered and concentrated under reduced pressure to provide crude 4-chloro-N-{5-chloro-2-[hydroxy-(2-nitro-phenyl)-methyl]-pyridin-3-yl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide, which was used in the following step without any purification. Mass spectrum m/z: 566.3 (M+H).

Workup

  1. stirringstirred for 3 h
  2. customIt was then quenched with saturated aqueous NH4Cl (2 mL)
  3. extractionextracted with EtOAc
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b51350378e8143b193cd3505c061e4cc
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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