Water → HCID 90051681, compound

HRID 2284806Notes

Reaction equation

HRID 2284806 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[C:5]([I:16])=[CH:4][N:3]=1.[CH2:17](I)[CH2:18][CH3:19].C(OCC)(=O)C.O>CN1CCCC1=O.[H-].[Na+]>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]([CH2:17][CH2:18][CH3:19])[C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[C:5]([I:16])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 336431-IodopropaneHCID 722069341259224-06-0

Product 1

HCID 90051681HCID 90051681, compound

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of tert-butyl (2-chloro-5-iodopyridin-4-yl)carbamate (S8, 239 mg) and propyl iodide (131 μL) in N-methylpyrrolidone (3 mL), sodium hydride (60% wt, 80 mg) was added under ice cooling, and the mixture was stirred at room temperature for 2 hours, and then stirred at 50° C. for 3 hours. The reaction mixture was cooled to room temperature, and then ethyl acetate and water were added to the reaction mixture. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (eluent, 100 to 70% hexane in ethyl acetate) to obtain tert-butyl (2-chloro-5-iodopyridin-4-yl)(propyl)carbamate (S9, 155 mg).

Workup

  1. stirringstirred at 50° C. for 3 hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe organic layer was separated
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (eluent, 100 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-bffba2d216604710a6c507cfcdecafa3
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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