2,6-Dibromopyridine → HCID 23144486, compound

HRID 337462Notes

Reaction equation

HRID 337462 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.C([Mg]Cl)(C)C.[O:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[C:19]1[N:20]=[C:21]([NH:30][C:31]([C:33]2[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=2)=[O:32])[S:22][C:23]=1[C:24](=[O:29])N(OC)C.[Cl-].[NH4+]>C1COCC1>[Br:8][C:4]1[N:3]=[C:2]([C:24]([C:23]2[S:22][C:21]([NH:30][C:31]([C:33]3[CH:34]=[CH:35][N:36]=[CH:37][CH:38]=3)=[O:32])=[N:20][C:19]=2[C:15]2[O:14][CH:18]=[CH:17][CH:16]=2)=[O:29])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 122742,6-DibromopyridineHCID 25517Ammonium ChlorideHCID 23144082HCID 23144082, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 23144486HCID 23144486, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A THF solution (10 mL) of 2,6-dibromopyridine (4.97 g, 21.0 mmol) was added to a 2.0 mol/L solution of isopropylmagnesium chloride in THF (9.56 mL, 10.1 mmol) at 0° C., followed by stirring for 3 hours at room temperature. A THF solution (5 mL) of Compound 98 (1.37 g, 3.82 mmol) was added dropwise to the reaction mixture, followed by stirring for 3 hours at room temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1) to afford the entitled Compound 300 (520 mg, 31%).

Workup

  1. stirringby stirring for 3 hours at room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled away under reduced pressure
  6. customThe resulting residue was purified through silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-2b461c98466e46eb93ee26481b1e5ffa
Source dataset
uspto-grants-2014_11
Patent number
US08889718B2

Reaction notes

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