3-Bromopyridine → HCID 18322227, compound

HRID 1698845Notes

Reaction equation

HRID 1698845 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][CH2:22][N:23]2[C:27](=[O:28])[C:26]3=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]3[C:24]2=[O:33])[CH:18]=[CH:19][CH:20]=1.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[OH:28][C:27]1([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[C:26]2[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:24](=[O:33])[N:23]1[CH2:22][CH2:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

7

Reactant 4

HCID 122863-BromopyridineHCID 25517Ammonium ChlorideHCID 18322222HCID 18322222, compoundHCID 178418339Butyllithium

Product 1

HCID 18322227HCID 18322227, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

At −70° C., a 1.6 M butyllithium solution (3.99 mmol) in absolute diethyl ether was admixed dropwise with a solution of 0.56 g (3.56 mmol) of 3-bromopyridine in absolute diethyl ether. The color of the mixture changed to yellow, and a precipitate was formed. After 1 h at −70° C., a solution of 0.5 g (1.78 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide in 10 ml of absolute tetrahydrofuran was added dropwise. The reaction mixture was warmed to room temperature, stirred for another 1 h and then admixed with 10 ml of saturated ammonium chloride solution. The mixture was extracted three times with diethyl ether. The combined organic phases were washed once with saturated sodium chloride solution, dried and evaporated to dryness using a rotary evaporator. The colorless oily crude product was purified by chromatography. Elution was carried out using a dichloromethane/methanol gradient (0 to 3% methanol). The resulting colorless oil solidified on standing at room temperature. Yield: 0.34 g. M.p.: 97° C.

Workup

  1. customAt −70° C.
  2. customwas formed
  3. extractionThe mixture was extracted three times with diethyl ether
  4. washThe combined organic phases were washed once with saturated sodium chloride solution
  5. customdried
  6. customevaporated to dryness
  7. customa rotary evaporator
  8. customThe colorless oily crude product was purified by chromatography
  9. washElution
  10. customon standing at room temperature

Sources & evidence

ORD record
ord-e401468b1c4f422b9311f5ad580dd96e
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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