2-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate → 6-Bromo-2,3-dihydroimidazo[1,2-a]pyridine-3-carbonitrile

HRID 1792458Notes

Reaction equation

HRID 1792458 reaction equation
C1(C)C=CC(S(O[CH:11]([C:21]#[N:22])[CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=2)(=O)=O)=CC=1>C(#N)C>[Br:20][C:17]1[CH:18]=[CH:19][C:14]2[N:15]([CH:11]([C:21]#[N:22])[CH2:12][N:13]=2)[CH:16]=1

Participants

3

Reactant 1

HCID 235374122-(5-Bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate

Product 1

HCID 220317966-Bromo-2,3-dihydroimidazo[1,2-a]pyridine-3-carbonitrileYield 88.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

7.64 g of 2-(5-bromo-2-pyridinylamino)-1-cyanoethyl toluene-4-sulfonate was dissolved in 76 mL acetonitrile, and the mixture was heated for 15 hours under reflux. After the solvent was removed, an aqueous saturated sodium bicarbonate was poured into the reaction product which was then extracted with dichloromethane, and the organic layer was dried over anhydrous sodium sulfate and filtered through NH silica gel. The solvent was removed, whereby 3.83 g of the title compound (yellow solid) was obtained.

Workup

  1. temperaturethe mixture was heated for 15 hours
  2. temperatureunder reflux
  3. customAfter the solvent was removed
  4. additionan aqueous saturated sodium bicarbonate was poured into the reaction product which
  5. extractionwas then extracted with dichloromethane
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered through NH silica gel
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-fa9d214665694c878069c3dfffe8226b
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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