Triethylamine → N-(5-Iodopyridin-2-yl)-2,2-dimethylpropanamide

HRID 2042177Notes

Reaction equation

HRID 2042177 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.CCN(CC)CC.[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18].C([O-])(O)=O.[Na+]>ClCCl>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 885792-Pyridinamine, 5-iodo-HCID 516892Sodium Bicarbonate

Product 1

HCID 17100900N-(5-Iodopyridin-2-yl)-2,2-dimethylpropanamideYield 106.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2.5 °C

Procedure

5-Iodopyridin-2-amine (5 g, 22.7 mmol) was dissolved in 50 ml of dichloromethane and Et3N (6.3 ml, 45.5 mmol, 2 equiv.) was added at room temperature. The mixture was cooled to 0-5° C. and pivaloyl chloride (3.4 ml, 27.3 mmol, 1.2 equiv.) was added dropwise. The reaction mixture was stirred for 1 hour at 0-5° C. Saturated NaHCO3-solution was added and the mixture was extracted with dichloromethane. The organic extracts were dried with sodium sulfate, filtered and evaporated to dryness. The desired N-(5-iodopyridin-2-yl)pivalamide (7.34 g, 99.8% yield) was obtained as a brown oil, MS: m/e=305.0 (M+H+).

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-40496945cf734859bf6371d45894cd0a
Source dataset
uspto-grants-2013_11
Patent number
US08586581B2

Reaction notes

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