Methyl iodide → 1-{[3-(methylsulfanyl)tricyclo[3.3.1.13,7]dec-1-yl]methyl}-1H-pyrazole

HRID 336622Notes

Reaction equation

HRID 336622 reaction equation
[N:1]1([CH2:6][C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][C:9]([SH:17])([CH2:10]4)[CH2:8]2)[CH2:14]3)[CH:5]=[CH:4][CH:3]=[N:2]1.[CH3:18][O-].[Na+].IC>CO>[CH3:18][S:17][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][C:7]([CH2:6][N:1]4[CH:5]=[CH:4][CH:3]=[N:2]4)([CH2:16]3)[CH2:8]1)[CH2:15]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10942334Sodium MethoxideHCID 894989493-(1H-pyrazol-1-ylmethyl)tricyclo[3.3.1.13,7]decane-1-thiol

Product 1

HCID 894985951-{[3-(methylsulfanyl)tricyclo[3.3.1.13,7]dec-1-yl]methyl}-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of EXAMPLE 81A (300 mg) in methanol (2 mL) was added sodium methoxide (4 mL, 0.5 M in methanol). Iodomethane (0.5 mL) was added, and the reaction heated to reflux for 3 hours. The reaction was cooled to room temperature and concentrated to dryness. The residue war purified by reverse phase HPLC, eluting with a gradient of 30% to 100% acetonitrile in water containing 0.1% v/v trifluoroacetic acid, to give the title product.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux for 3 hours
  3. concentrationconcentrated to dryness
  4. customThe residue war purified by reverse phase HPLC
  5. washeluting with a gradient of 30% to 100% acetonitrile in water containing 0.1% v/v trifluoroacetic acid

Sources & evidence

ORD record
ord-b863e7b56a574b03af38f1f04dfa5b1f
Source dataset
uspto-grants-2014_11
Patent number
US08889675B2

Reaction notes

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