2-Bromopyridine → HCID 22181068, compound

HRID 1796201Notes

Reaction equation

HRID 1796201 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.Br[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N+:15]([O-:17])=[O:16])[CH:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 79732-BromopyridineHCID 22181052HCID 22181052, compound

Product 1

HCID 22181068HCID 22181068, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 3-chloro-4-(piperidin-4-yloxy)nitrobenzene (3.00 g) obtained in reference example 8 in pyridine (30 ml) was added 2-bromopyridine (1.25 ml) at room temperature, and the resulting mixture was stirred at 150° C. for 16 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:2) as the eluent to afford the title compound (0.80 g, yield: 20%) as a yellow solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue obtained
  6. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-fb136cea15524a588eec33bf8a0ece06
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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