HCID 86758853, compound → HCID 18629424, compound

HRID 1060888Notes

Reaction equation

HRID 1060888 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[N:10][S:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:5][C:4]=1[F:23])#[N:2].[CH3:24][Mg+].[Br-]>C1COCC1>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([NH:10][S:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[O:12])([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH3:24])=[CH:5][C:4]=1[F:23])#[N:2]

Participants

4

Reactant 2

HCID 86758853HCID 86758853, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 18629424HCID 18629424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[(4-cyano-3-fluoro-phenyl)-(3-pyridyl)-methylene]-2-methylpropanesulfinamide (0.315 g, 0.956 mmol) was dissolved in anhydrous THF (10 mL), cooled in a ice bath, and treated with a 3.0 M ethereal solution of MeMgBr (0.96 mL, 2.87 mmol). After 15 min, the reaction was quenched with H2O, diluted with CH2Cl2 and saturated NaHCO3 solution and separated. The aqueous layer was extracted with CH2Cl2 (2×), the organic layers combined, dried (Na2SO4), filtered and concentrated to give the title compound after chromatography on a Waters Prep Pak column eluting with 0.1% TFA/H2O: 0.1% TFA/CH3CN, 95:5 to 5:95.

Workup

  1. temperaturecooled in a ice bath
  2. customthe reaction was quenched with H2O
  3. additiondiluted with CH2Cl2 and saturated NaHCO3 solution
  4. customseparated
  5. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-67056d98d94d4000b7564df9f872a58a
Source dataset
uspto-grants-2003_02
Patent number
US06525074B2

Reaction notes

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