HCID 87094779, compound → HCID 66661070, compound

HRID 1909109Notes

Reaction equation

HRID 1909109 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[N:9]/[S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[N:6][CH:7]=1.[CH3:16][Mg]Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:9][S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])[CH3:16])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 87094779HCID 87094779, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66661070HCID 66661070, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[(1E)-(5-fluoropyridin-2-yl)methylene]-2-methylpropane-2-sulfinamide (52.12 g, 228 mmol) in dichloromethane (1000 mL) at −78° C. was added methylmagnesium bromide (3.0 M in THF; 198 mL, 594 mmol). The mixture was allowed to warm to ambient temperature. After 30 min, the mixture was cooled down to −78° C. and was quenched with saturated aqueous ammonium chloride (100 mL). The mixture was allowed to warm to ambient temperature. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×). The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% ethyl acetate) gave the title compound. MS 245 (M+1).

Workup

  1. temperaturethe mixture was cooled down to −78° C.
  2. customwas quenched with saturated aqueous ammonium chloride (100 mL)
  3. temperatureto warm to ambient temperature
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (3×)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by silica gel chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-502df4def060459e96ee4567626592e7
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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