Pyridine → HCID 58316712, compound

HRID 1426231Notes

Reaction equation

HRID 1426231 reaction equation
O[NH:2][C:3](=[N:8][C:9]1[CH:14]=[CH:13][C:12]([I:15])=[CH:11][N:10]=1)[C:4]([CH3:7])([CH3:6])[CH3:5].N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[C:4]([C:3]1[N:8]=[C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][N:10]2[N:2]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 58316723HCID 58316723, compound

Product 1

HCID 58316712HCID 58316712, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

N-Hydroxy-N′-(5-iodo-pyridin-2-yl)-2,2-dimethyl-propionamidine (example 39, step 3) (2.8 g, 8.77 mmol) was suspended in 15 ml of toluene and pyridine (2.8 ml, 35.1 mmol, 4 equiv.). The mixture was cooled to 0-5° C. and p-toluenesulfonyl chloride (6.7 g, 35.1 mmol, 4 equiv.) was added. The reaction mixture was stirred for 1 hour at 0-5° C. and 4 hours at room temperature. The reaction mixture was extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a 20 g silica gel column and eluting with heptane:ethyl acetate 100:0→0:100. The desired 2-tert-butyl-6-iodo-[1,2,4]triazolo[1,5-a]pyridine (2 g, 76% yield) was obtained as a light yellow oil, MS: m/e=302.1 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with saturated NaHCO3 solution and two times with a small volume of dichloromethane
  2. customThe crude product was purified by flash chromatography
  3. washeluting with heptane:ethyl acetate 100:0→0:100

Sources & evidence

ORD record
ord-d16bbcbfca2e42739b454854d4e05f15
Source dataset
uspto-grants-2015_01
Patent number
US08933094B2

Reaction notes

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