Triethylamine → 2-Ethenyl-5-nitropyridine

HRID 1519515Notes

Reaction equation

HRID 1519515 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]([B-](F)(F)F)=[CH2:12].[K+].C(N(CC)CC)C>C(O)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:11]=[CH2:12])=[N:3][CH:4]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 782402-Bromo-5-nitropyridineHCID 23679353Potassium vinyltrifluoroborate

Product 1

HCID 230905502-Ethenyl-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a 20 ml, microwave tube was added 2-bromo-5-nitropyridine (0.20 g, 0.98 mmol), potassium vinyltrifluoroborate (145 mg, 1.1 mmol), PdCl2(dppf)-CH2Cl2 complex (40 mg, 0.049 mmol), and a stir bar. The tube was sealed, and ethanol (6 mL) and triethylamine (0.41 mL, 3.0 mmol) was added via syringe. The mixture was purged three times with nitrogen and then heated to 120° C. for 30 minutes. LC at that point showed mostly product. The reaction was diluted with DCM, adsorbed onto silica gel, and purified by silica gel flash chromatography (Hexane:EtOAc). LC-MS (IE, m/z): 151 [M+1]+.

Workup

  1. customThe tube was sealed
  2. customThe mixture was purged three times with nitrogen
  3. additionThe reaction was diluted with DCM
  4. custompurified by silica gel flash chromatography (Hexane:EtOAc)

Sources & evidence

ORD record
ord-d3df7ab4e8044fd197f9680fa6f818f3
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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