Methyl iodide → 3-(5-((methylthio)methyl)furan-2-yl)pyridine

HRID 1913349Notes

Reaction equation

HRID 1913349 reaction equation
[C:1](=O)([S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)C.C[O-].[Na+].CI.C(=O)(O)[O-].[Na+]>CO>[CH3:1][S:3][CH2:4][C:5]1[O:6][C:7]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 11993872S-(5-(Pyridin-3-yl)furan-2-yl)methyl ethanethioate

Product 1

HCID 119938733-(5-((methylthio)methyl)furan-2-yl)pyridineYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

(See FIG. 7.) To a solution of 13 (27 mg, 0.12 mmol) in anhydrous CH3OH (3 mL) at 0° C. under argon was added a solution of sodium methoxide (15 mg, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise, over 10 min and the resultant solution was stirred for 30 min. To the solution was added methyl iodide (17 μL, 0.28 mmol) in anhydrous CH3OH (1 mL) dropwise over 1 min and the resultant solution was stirred for 30 min. The reaction was stopped by the addition of aqueous sodium bicarbonate (satd. soln., 10 mL). The CH3OH was removed in vacuo and the aqueous fraction was extracted with EtOAc (3×10 mL). The combined organic fractions were dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2) to afford the title compound 15 (13 mg, 54% yield) as an off white solid: mp=67-68° C.; 1H NMR (CDCl3) δ 8.90 (br s, 1H), 8.46 (m, 1H), 7.90 (m, 1H), 7.29 (m, 1H), 6.66 (d, J=3.3 Hz, 1H), 6.29 (d, J=3.3 Hz, 1H), 3.74 (s, 2H), 2.14 (s, 3H); LRMS (ESI) m/z calcd for C11H12NOS [M+H]+ 206. found 206.

Workup

  1. customThe CH3OH was removed in vacuo
  2. extractionthe aqueous fraction was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.2)

Sources & evidence

ORD record
ord-3d710a995b4e42999e5f51094cc7427a
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

Loading…