Potassium Carbonate → HCID 79039990, compound

HRID 1392917Notes

Reaction equation

HRID 1392917 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[N:3]=1.[CH3:10][O:11][CH2:12][CH2:13][NH:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([CH2:8][N:14]([CH2:13][CH2:12][O:11][CH3:10])[CH3:15])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 300977(2-Methoxyethyl)(methyl)amineHCID 220327372-(Bromomethyl)-6-chloro-pyridine

Product 1

HCID 79039990HCID 79039990, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-chloro-6-(bromomethyl)pyridine (490 mg, 2.37 mmole) in 5 mL of dry acetonitrile is added 0.51 mL (4.74 mmol) of 2-methoxy-N-methylethylamine and 328 mg (2.37 mmol) of potassium carbonate. The reaction is heated at 80° C. for 2 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three-times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 478 mg (94% yield) of (6-Chloro-pyridin-2-ylmethyl)-(2-methoxy-ethyl)-methyl-amine. Diagnostic 1H NMR (400 MHz, CDCl3) 2.34 (s, 3h), 2.67 (t, 2H, J=5.9 Hz), 3.34 (s, 3H), 3.52 (t, 2H, J=5.8 Hz), 3.71 (s, 3H), 7.19 (d, 1H, J=7.9 Hz), 7.54 (d, 1H, J=7.9 Hz), 7.60–7.64 (m, 1H); MS 215.2 (M+H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture is quenched with 5 mL of water
  3. extractionextracted three-times with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customConcentration of the solvent provided an oil which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-96b8f1346b49498c90dc7df0f3444218
Source dataset
uspto-grants-2008_03
Patent number
US07345038B2

Reaction notes

Loading…