Methyl iodide → HCID 53244675, compound

HRID 1424693Notes

Reaction equation

HRID 1424693 reaction equation
CI.[CH3:3][O:4][C:5]1[C:6]2[N:7]([N:12]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[NH:20][CH:21]=3)[N:14]=2)[C:8]([CH3:11])=[CH:9][CH:10]=1.[C:28]([O-])([O-])=O.[Cs+].[Cs+]>CC(=O)CC>[CH3:3][O:4][C:5]1[C:6]2[N:7]([N:12]=[C:13]([CH2:15][CH2:16][C:17]3[N:18]=[C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:20]([CH3:28])[CH:21]=3)[N:14]=2)[C:8]([CH3:11])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178490911HCID 178490911, compound

Product 1

HCID 53244675HCID 53244675, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
50 °C

Procedure

Methyl iodide (0.035 mL, 0.57 mmol) was added to a stirred suspension of 8-Methoxy-5-methyl-2-[2-(2-phenyl-1H-imidazol-4-yl)-ethyl]-[1,2,4]triazolo[1,5-a]pyridine (145 mg, 0.435 mmol) and Cs2CO3 (360 mg, 1.1 mmol) in 2-Butanone (10 mL). The mixture was heated at 50° C. for 7 hours under an atmosphere of Argon. The mixture was cooled to rt and the solvent was evaporated off. The crude product was dissolved in DCM and purified by silica gel chromatography (Eluent: 0-100% EtOAc in n-heptane, then changed to 0-5% MeOH in EtOAc). Yield: 31 mg (20%) of the title compound as an off white solid. LC-MS: m/z=348.2 (MH+), tR=0.70 min, method E.

Workup

  1. temperatureThe mixture was cooled to rt
  2. customthe solvent was evaporated off
  3. dissolutionThe crude product was dissolved in DCM
  4. custompurified by silica gel chromatography (Eluent

Sources & evidence

ORD record
ord-3ab73aa0301a403a88ffe15f2150393c
Source dataset
uspto-grants-2015_01
Patent number
US08927738B2

Reaction notes

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