Pyridine → HCID 59321155, compound

HRID 341219Notes

Reaction equation

HRID 341219 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[C:3]([NH:5][NH:6][C:7]([C:9]1[CH:14]=[CH:13][N:12]2[C:15]([I:18])=[CH:16][N:17]=[C:11]2[CH:10]=1)=[O:8])=O.N1C=CC=CC=1.S(Cl)(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[C:2]([C:3]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][N:12]3[C:15]([I:18])=[CH:16][N:17]=[C:11]3[CH:10]=2)=[N:6][N:5]=1)([CH3:20])([CH3:19])[CH3:1]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 593207903-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid N'-(2,2-dimethylpropionyl) hydrazide

Product 1

HCID 59321155HCID 59321155, compoundYield 8.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

3-Iodo-imidazo[1,2-a]pyridine-7-carboxylic acid N′-(2,2-di methyl propionyl) hydrazide (875 mg, 2.27 mmol) was suspended in anhydrous THF (15 mL) under a nitrogen atmosphere. Pyridine (0.388 mL, 4.76 mmol) and tosyl chloride (518 mg, 2.72 mmol) were added and the mixture was heated to 70° C. overnight. The reaction was cooled and partitioned between EtOAc and 1M HCl. The aqueous fraction was basified with 2M sodium carbonate solution and extracted with CH2Cl2. The organic phase was dried through a phase separation cartridge and evaporated to give 7-(5-tert-Butyl-[1,3,4]-oxadiazol-2-yl)-3-iodo-imidazo[1,2-a]pyridine (70 mg) as a white solid.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between EtOAc and 1M HCl
  3. extractionextracted with CH2Cl2
  4. customThe organic phase was dried through a phase separation cartridge
  5. customevaporated

Sources & evidence

ORD record
ord-f7c9678716f34ae9a1a673025af09c86
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Reaction notes

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