HCID 57942263, compound → HCID 57942413, compound

HRID 1898101Notes

Reaction equation

HRID 1898101 reaction equation
Br[C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[C:4]([CH3:27])[N:3]=1.C([Mg]Cl)(C)C.CON(C)[C:36](=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43][CH3:44]>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([N:8]([C:7]2[C:2]([C:36](=[O:45])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[S:43][CH3:44])=[N:3][C:4]([CH3:27])=[C:5]([Cl:26])[CH:6]=2)[CH2:23][O:24][CH3:25])(=[O:11])=[O:10])=[CH:13][C:14]=1[C:19]([F:22])([F:21])[F:20]

Participants

5

Reactant 3

HCID 57942263HCID 57942263, compoundHCID 57942589HCID 57942589, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57942413HCID 57942413, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-(2-bromo-5-chloro-6-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (255 mg, 0.5 mmol) in anhydrous THF (3 mL) was added 2 M isopropylmagnesiumchloride in THF (600 L, 1.2 mmol) at −40° C. It was then warmed to 0° C. and stirred at the same temperature for 1 h and then N-Methoxy-N-methyl-2-methylsulfanyl-benzamide (422 mg, 1.00 mmol) was added in and the progress of the reaction was followed by LCMS. The reaction mixture was warmed to room temperature and stirred overnight (18 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. The residue was purified by flash column chromatography (ISCO) to provide 4-chloro-N-[5-chloro-6-methyl-2-(2-methylsulfanyl-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide. Mass spectrum m/z: 601.4 (M+Na).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred overnight (18 h)
  3. customIt was then quenched with saturated aqueous NH4Cl (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography (ISCO)

Sources & evidence

ORD record
ord-f56506891b0446ea9b064fb95437f207
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

Loading…