Triethylamine → 7-[5-Nitro-6-(trifluoromethyl)-2-pyridyl]-7-azabicyclo[2.2.1]heptane

HRID 869496Notes

Reaction equation

HRID 869496 reaction equation
Br[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.Cl.[CH:16]12[NH:22][CH:19]([CH2:20][CH2:21]1)[CH2:18][CH2:17]2.C(N(CC)CC)C>C(#N)C>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([N:22]2[CH:16]3[CH2:21][CH2:20][CH:19]2[CH2:18][CH2:17]3)=[N:7][C:6]=1[C:8]([F:11])([F:10])[F:9])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 162795037-Azabicyclo[2.2.1]heptane hydrochlorideHCID 593162396-Bromo-3-nitro-2-(trifluoromethyl)pyridine

Product 1

HCID 593162357-[5-Nitro-6-(trifluoromethyl)-2-pyridyl]-7-azabicyclo[2.2.1]heptaneYield 94.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 6-bromo-3-nitro-2-(trifluoromethyl)pyridine (300 mg, 1.107 mmol), 7-azabicyclo[2.2.1]heptane hydrochloride (177.4 mg, 1.328 mmol) and triethylamine (224.0 mg, 308.5 μL, 2.214 mmol) in acetonitrile (3 mL) was heated at 80° C. overnight. The reaction was cooled to room temperature and quenched with water. The resulting precipitate was filtered, washed with water and dried under vacuum to provide 7-[5-nitro-6-(trifluoromethyl)-2-pyridyl]-7-azabicyclo[2.2.1]heptane (300 mg, 94% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 8.27 (d, J=9.2 Hz, 1H), 7.20 (d, J=9.3 Hz, 1H), 4.71 (s, 2H), 1.71 (d, J=7.7 Hz, 4H), 1.55 (d, J=6.9 Hz, 4H).

Workup

  1. customquenched with water
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-fda8ec119ddb48eb9e19f41cdb369fa0
Source dataset
uspto-grants-2015_03
Patent number
US08969382B2

Reaction notes

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