N-Iodosuccinimide → HCID 178451661, compound

HRID 340072Notes

Reaction equation

HRID 340072 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][CH:15]=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([I:24])C(=O)C1>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[NH:14][C:15]([I:24])=[N:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 178451662HCID 178451662, compound

Product 1

HCID 178451661HCID 178451661, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,4,6,7-tetrahydro-imidazo[4,5-c]pyridine-5-carboxylic acid tert-butyl ester (Preparation 20, 18 g, 80.62 mmol) in THF (300 mL) was added NIS (27.2 g, 121 mmol). The reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with EtOAc (800 mL), washed with sodium thiosulfate aqueous solution (3×700 mL) and brine (500 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a yellow solid (18.25 g) in a 64.8% yield.

Workup

  1. washwashed with sodium thiosulfate aqueous solution (3×700 mL) and brine (500 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de168fe70727497791026636cd37d88c
Source dataset
uspto-grants-2014_11
Patent number
US08895544B2

Reaction notes

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