2-Aminopyridine → HCID 21699770, compound

HRID 1597621Notes

Reaction equation

HRID 1597621 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C.CCOC(C)=O>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 24758Sodium hydrideHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 21699770HCID 21699770, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-Aminopyridine (3-1, 1.97 g, 20.9 mmol) in 10 mL DMF was added to a suspension of NaH (60% in oil, 1.00 g, 25 mmol) in 80 mL DMF cooled to 0° C. After warming to RT for 45 min, ethyl 5-bromopentanoate (4.2 mL, 25 mmol) was added dropwise. This mixture was heated at 75° C. overnight, then cooled to RT, diluted with EtOAc, washed with water (2×), sat. NaHCO3, and brine, dried (MgSO4), filtered and concentrated. Flash chromatography (silica, 50% then 70% EtOAc/hexane) provided 3-2 as a yellow oil.

Workup

  1. temperatureAfter warming to RT for 45 min
  2. temperatureThis mixture was heated at 75° C. overnight
  3. temperaturecooled to RT
  4. washwashed with water (2×), sat. NaHCO3, and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8e750caed6644049b9649beb17a6942
Source dataset
uspto-grants-2001_09
Patent number
US06294549B1

Reaction notes

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