Methyl iodide → N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-N-methyl-methanesulfonamide

HRID 472479Notes

Reaction equation

HRID 472479 reaction equation
[Cl:1][C:2]1[N:23]=[C:5]2[C:6]([C:10]#[C:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[C:24](=O)([O-])[O-].[Cs+].[Cs+].IC>C(#N)C>[Cl:1][C:2]1[N:23]=[C:5]2[C:6]([C:10]#[C:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:18]([CH3:24])[S:19]([CH3:22])(=[O:21])=[O:20])=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 67478887N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-methanesulfonamide

Product 1

HCID 67478783N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-N-methyl-methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

189 c) To a suspension of N-[2-(2-chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-methanesulfonamide (900.0 mg, 2.595 mmol) and cesium carbonate (950.0 mg, 2.916 mmol) in acetonitrile (5 mL) was added iodomethane (0.25 mL, 4.0 mmol). The reaction flask was capped and the mixture was stirred at room temperature over weekend. The volatiles were evaporated. The recovered solid was triturated with water (30 mL), filtered and rinsed with water then was dissolved in dichloromethane (50 mL) and was separated. The organic layer was dried over magnesium sulfate, filtered and evaporated. N-[2-(2-Chloro-[1,2,4]triazolo[1,5-a]pyridin-8-ylethynyl)-phenyl]-N-methyl-methanesulfonamide was isolated as a tan solid (0.871 g, 93%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.51 (d, J=6.7 Hz, 1H), 7.78 (d, J=7.4 Hz, 1H), 7.68 (d, J=7.6 Hz, 1H), 7.52 (d, J=7.8 Hz, 1H), 7.46 (t, J=7.4 Hz, 1H), 7.38 (t, J=7.5 Hz, 1H), 7.10 (t, J=7.1 Hz, 1H), 3.54 (s, 3H), 3.21 (s, 3H). MS=361, 363 (MH)+.

Workup

  1. customThe reaction flask was capped
  2. customThe volatiles were evaporated
  3. customThe recovered solid was triturated with water (30 mL)
  4. filtrationfiltered
  5. washrinsed with water
  6. dissolutionthen was dissolved in dichloromethane (50 mL)
  7. customwas separated
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-8ccdef037107411c9da76ae88d971e43
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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