Methyl iodide → 5-Methyl-2-(2-methyl-5-phenyl-2H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1627737Notes

Reaction equation

HRID 1627737 reaction equation
CI.[CH3:3][C:4]1[N:9]2[N:10]=[C:11]([CH2:13][S:14][C:15]3[NH:16][N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1.[C:26](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:3][C:4]1[N:9]2[N:10]=[C:11]([CH2:13][S:14][C:15]3[N:16]([CH3:26])[N:17]=[C:18]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[N:19]=3)[N:12]=[C:8]2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1784239795-Methyl-2-(5-phenyl-2H-1,2,4-triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 672573505-Methyl-2-(2-methyl-5-phenyl-2H-[1,2,4]triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Methyl iodide (142 mg, 1.00 mmol) dissolved in DMF (0.5 ml) was added to a stirred suspension of 5-Methyl-2-(5-phenyl-2H-1,2,4-triazol-3-ylsulfanylmethyl)-[1,2,4]triazolo[1,5-a]pyridine (322 mg, 1.00 mmol) and Potassium carbonate (276 mg, 2.0 mmol) in N,N-Dimethylformamide (3.5 mL) at rt, under Ar. The solution was stirred at 3 h and then quenched by adding Sat bicarbonate sol and extracting with EtOAc. The Organic phase was dried (MgSO4) and was rotovaped. The crude product was purified by HPLC. This afforded 10 mg of the title compound. LC-MS: m/z=337.1 (MH+), tR=0.63 min, Method B. 1H NMR (600 MHz, DMSO-d6): δ 7.96 (d, 2H), 7.63 (d, 1H), 7.60 (t, 1H) 7.50-7.40 (m, 3H), 7.07 (d, 1H), 4.68 (s, 2H), 2.66 (s, 3H).

Workup

  1. customquenched
  2. additionby adding Sat bicarbonate sol
  3. extractionextracting with EtOAc
  4. dry with materialThe Organic phase was dried (MgSO4)
  5. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-f9da78f2f6cd4b8d935afae795e3435f
Source dataset
uspto-grants-2014_07
Patent number
US08785653B2

Reaction notes

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