Sulfuric acid magnesium salt (1:1) → HCID 16738347, compound

HRID 910209Notes

Reaction equation

HRID 910209 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([C:15]#N)=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1.[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+].S([O-])([O-])(=O)=[O:32].[Mg+2]>C(OCC)C.ClCCl.O1CCCC1>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]3[CH:18]=[CH:17][C:14]([CH:15]=[O:32])=[CH:13][CH:12]=3)[N:10]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 21225700DiisobutylaluminumhydrideHCID 67405072HCID 67405072, compound

Product 1

HCID 16738347HCID 16738347, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(6-Iodoimidazo[1,2-a]pyridin-2-yl)benzonitrile (1.27 g) was added to a mixture of tetrahydrofuran (15 mL) and dichloromethane (15 mL), followed by stirring under ice cooling. Diisobutylaluminum hydride (7.8 mL) was added dropwise to the reaction mixture, and the resultant mixture was stirred at the same temperature for 15 minutes and then at room temperature for 4 hours. Aqueous saturated ammonium chloride solution (2 mL) was added dropwise to the reaction mixture, followed by stirring at room temperature for 1 hour. Subsequently, magnesium sulfate and diethyl ether were added to the reaction mixture, followed by further stirring for 1 hour. The solvent was evaporated, and the residue was purified through silica gel column chromatography (dichloromethane:methanol=95:5). The purified product was concentrated under reduced pressure, to thereby yield the title compound (1.03 g).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. stirringby further stirring for 1 hour
  3. customThe solvent was evaporated
  4. customthe residue was purified through silica gel column chromatography (dichloromethane:methanol=95:5)
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-48ef9eb61a604ba3bcac228c29df0d23
Source dataset
uspto-grants-2011_09
Patent number
US08022075B2

Reaction notes

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