Dimethyl Sulfide → 3-Methylsulfanyl-5-phenylethynylpyridine

HRID 606903Notes

Reaction equation

HRID 606903 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1.C(N(CC)CC)C.[CH3:28][S:29]C>O1CCCC1.O>[CH3:28][S:29][C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 670476693-Bromo-5-phenylethynylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 670478293-Methylsulfanyl-5-phenylethynylpyridineYield 2.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Add a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran (0.96 mL, 1.94 mmol) to a solution of 3-bromo-5-phenylethynylpyridine, (prepared as described in EXAMPLE 9), (500 mg, 1.94 mmol) in anhydrous tetrahydrofuran (2 mL) and stir under nitrogen at room temperature for 2 h. Add triethylamine (0.27 mL, 1.94 mmol) and dimethyl sulfide (0.175 mL, 1.94 mmol). Stir for an additional 2 h, dilute with water, extract with dichloromethane, dry (magnesium sulfate), filter and concentrate. Purify the residue by silica gel chromatography, eluting from 100:0 to 100:50 with hexanes:ethyl acetate, to give the title compound (10.1 mg, 2.3%).

Workup

  1. stirringStir for an additional 2 h
  2. extractionextract with dichloromethane
  3. dry with materialdry (magnesium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify the residue by silica gel chromatography
  7. washeluting from 100:0 to 100:50 with hexanes

Sources & evidence

ORD record
ord-0c0c4ff396744c1bb68e3b8a3186b30c
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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