Triethylamine → HCID 66936980, compound

HRID 1963876Notes

Reaction equation

HRID 1963876 reaction equation
F[C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[N:3]=1.[F:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)[CH2:14][NH2:15].C(N(CC)CC)C>CN1C(=O)CCC1>[F:8][C:7]1[C:2]([NH:15][CH2:14][C:13]2[CH:16]=[CH:17][CH:18]=[C:11]([F:10])[CH:12]=2)=[N:3][C:4]([F:9])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 668533-FluorobenzylamineHCID 27832882,3,6-Trifluoropyridine

Product 1

HCID 66936980HCID 66936980, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

2,3,6-trifluoropyridine (1.07 mL, 1.5 g, 11.27 mmol), 3-fluorobenzylamine (3.18 mL, 3.53 g, 28.2 mmol), and triethylamine (4.71 mL, 3.42 g, 33.8 mmol) were dissolved in NMP (39 mL) to form a mixture This mixture reaction mixture was stirred at 100° C. for 1 hr. The reaction mixture was then extracted with EtOAc (3×75 mL). The combined extracts were washed with H2O (4×75 mL) followed by brine (1×75 mL). The organic layer was dried (Na2SO4), filtered, and the solvent removed in vacuo. The resulting residue was subjected to silica gel column chromatography. Elution using 100 hexanes to 30 EtOAc/70 hexanes yielded 2.63 g (98%) of 3,6-difluoro-N-(3-fluorobenzyl)pyridine-2-amine. LCMS (m/z): 239.1 (MH+), retention time=1.01 min.

Workup

  1. customto form a mixture
  2. customThis mixture reaction mixture
  3. extractionThe reaction mixture was then extracted with EtOAc (3×75 mL)
  4. washThe combined extracts were washed with H2O (4×75 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. washElution

Sources & evidence

ORD record
ord-16c5d33023a04750976a0cd9c75fcbf6
Source dataset
uspto-grants-2013_04
Patent number
US08415381B2

Reaction notes

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