Water → 6-Bromoimidazo[1,2-a]pyridine-3-carbonitrile

HRID 1792460Notes

Reaction equation

HRID 1792460 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](I)=[CH:9][N:10]=2)[CH:7]=1.C([Mg]Br)(C)C.C1(C)C=CC(S([C:26]#[N:27])(=O)=O)=CC=1.O>O1CCCC1.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:26]#[N:27])=[CH:9][N:10]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 87946p-Toluenesulphonyl cyanideHCID 220316326-Bromo-3-iodoimidazo(1,2-a)pyridineHCID 178418365HCID 178418365, compound

Product 1

HCID 220310786-Bromoimidazo[1,2-a]pyridine-3-carbonitrileYield 71.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Method 2) 80 g of 6-bromo-3-iodoimidazo[1,2-a]pyridine (compound in Production Example 49) was dissolved in 500 mL tetrahydrofuran, and 273 mL of 1.0 M isopropyl magnesium bromide in tetrahydrofuran was slowly added dropwise thereto at 0° C. and stirred for 30 minutes, and 380 mL of 68 g 4-toluenesulfonyl cyanide in tetrahydrofuran was added dropwise slowly over 1 hour, and the mixture was stirred for additional 1.5 hours. The reaction solution was poured into iced water, diluted with ethyl acetate and filtered through Celite. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate, and the collected organic layer was washed with brine. The organic layer was dried over anhydrous sodium sulfate and filtered through NH silica gel. Solid obtained by removing the solvent was triturated with diethyl ether, collected by filtration and washed with hexane to give 39.4 g of the title compound (brown solid).

Workup

  1. stirringthe mixture was stirred for additional 1.5 hours
  2. filtrationfiltered through Celite
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washthe collected organic layer was washed with brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered through NH silica gel
  8. customSolid obtained
  9. customby removing the solvent
  10. customwas triturated with diethyl ether
  11. filtrationcollected by filtration
  12. washwashed with hexane

Sources & evidence

ORD record
ord-7c7fbe84916a4ebe8d9ff238d3978720
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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