HCID 12171907, compound → HCID 86668957, compound

HRID 877348Notes

Reaction equation

HRID 877348 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[N:9]/[S:10]([C:12]([CH3:15])([CH3:14])[CH3:13])=[O:11])=[CH:4][CH:3]=1.Br[Mg][C:18]#[CH:19]>C(Cl)Cl.C1COCC1>[Br: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])[C:18]#[CH:19])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 12171907HCID 12171907, compoundHCID 178418486HCID 178418486, compound

Product 1

HCID 86668957HCID 86668957, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.8 g (9.7 mmol) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide in 30 ml CH2Cl2 at −78° C. was added 49 mL (24 mmol) 0.5M bromo(ethynyl)magnesium in THF. The reaction mixture was warmed slowly to room temperature. After 24 h at room temperature, the reaction mixture was quenched with saturated ammonium chloride, extracted three times with methylene chloride, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-100% EtOAc:hexane) afforded N-[(1R)-1-(4-bromophenyl)prop-2-ynyl]-2-methylpropane-2-sulfinamide. 1H NMR (CDCl3, 400 MHz) 7.52-7.45 (m, 2H); 7.41-7.38 (m, 2H); 5.19 (dd, 1H, J=2.38 Hz, 6.05 Hz); 3.66 (br d, 1H, J=6.04 Hz); 2.64 (d, 1H, J=2.38 Hz); 1.20 (s, 9H). ESMS+1=316.0.

Workup

  1. customthe reaction mixture was quenched with saturated ammonium chloride
  2. extractionextracted three times with methylene chloride
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over NaSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica gel, linear gradient 0-100% EtOAc:hexane)

Sources & evidence

ORD record
ord-fa52e8b9d9f9452fbf53df8bce9fdd60
Source dataset
uspto-grants-2015_03
Patent number
US08987310B2

Reaction notes

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