Methyl iodide → HCID 10968303, compound

HRID 394594Notes

Reaction equation

HRID 394594 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[N:18]=[N:19][NH:20][CH:21]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.IC.[C:24](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]4[CH:21]=[N:20][N:19]([CH3:24])[N:18]=4)=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505846HCID 178505846, compound

Product 1

HCID 10968303HCID 10968303, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-5-triazol-4-yl-1H-indole (6.0 g), iodomethane (6.7 mL), potassium carbonate (6.0 g) and acetone (100 mL) was boiled under weak reflux for 18 hours. The reaction mixture was filtered and the volatile solvents evaporated in vacuo. The mixture of 1-methyl- and 2-methyl-substituted triazoles was separated by column chromatography on silica gel (ethyl acetate/heptane 1:1). Evaporation of the fastest eluting fractions in vacuo afforded pure 1-(4-fluorophenyl)-5-(2-methyltriazol-4-yl)-1H-indole (20a) as an oil: (2.1 g): 1H NMR (CDCl3) δ 4.25 (s, 3H), 6.70 (d, 1H), 7.20 (t, 2H), 7.30 (d, 1H), 7.40-7.55 (m, 3H), 7.65 (broad d, 1H), 7.85 (s, 1H), 8.10 (broad s, 1H). Evaporation of the slowest eluting fractions in vacuo afforded pure 1-(4-fluorophenyl)-5-(1-methyltriazol-4-yl)-1H-indole (20b) as an oil (0.8 g): 1H NMR (CDCl3) δ 4.15 (s, 3H), 6.70 (d, 1H), 7.20 (t, 2H), 7.30 (d, 1H), 7.50 (dd, 2H), 7.55 (d, 1H), 7.70 (broad d, 1H), 7.75 (s, 1H), 8.10 (broad s, 1H).

Workup

  1. temperatureunder weak reflux for 18 hours
  2. filtrationThe reaction mixture was filtered
  3. customthe volatile solvents evaporated in vacuo
  4. additionThe mixture of 1-methyl- and 2-methyl-substituted triazoles
  5. customwas separated by column chromatography on silica gel (ethyl acetate/heptane 1:1)
  6. customEvaporation of the
  7. washfastest eluting fractions in vacuo

Sources & evidence

ORD record
ord-683be29d2afe432eb09625c3af8ae8c8
Source dataset
uspto-grants-2003_08
Patent number
US06602889B1

Reaction notes

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