Sodium methanethiolate → HCID 15490822, compound

HRID 1871354Notes

Reaction equation

HRID 1871354 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](Br)[CH:5]=[CH:4][C:3]=1[N:9]([CH2:27][CH3:28])[C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])[CH:13]=[C:12]([CH3:26])[N:11]=1.[CH3:29][S-:30].[Na+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([S:30][CH3:29])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:27][CH3:28])[C:10]1[N:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([F:25])([F:24])[F:23])[CH:13]=[C:12]([CH3:26])[N:11]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 18691320HCID 18691320, compound

Product 1

HCID 15490822HCID 15490822, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The product from Example 15 (450 mg), dimethylsulfoxide (12 mL), tetrakis(triphenylphosphine)Pd(0) (40 mg), and sodium thiomethoxide (61 mg) were heated at reflux 18 hours. The reaction was cooled, taken up and partitioned between ethyl acetate (100 mL) and water (100 mL). The ethyl acetate was washed with brine, dried over MgSO4, and concentrated to dryness. The crude product was chromatographed on silica gel giving the title compound (90 mg). CI-HRMS calcd. for C21H20N3F3SBr (M+H)+ : 482.051340. Found: 482.051434.

Workup

  1. temperatureat reflux 18 hours
  2. temperatureThe reaction was cooled
  3. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product was chromatographed on silica gel giving the title compound (90 mg)

Sources & evidence

ORD record
ord-0bfd55d3dff24ea6b0222ec1ed758f26
Source dataset
uspto-grants-2000_08
Patent number
US06103737

Reaction notes

Loading…