Pyrrolidine → HCID 178419330, compound

HRID 2112824Notes

Reaction equation

HRID 2112824 reaction equation
Br[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([Br:11])=[CH:10][C:4]=2[N:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C(#N)C>[Br:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[N:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 178419321HCID 178419321, compound

Product 1

HCID 178419330HCID 178419330, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of 1 g (3.6 mmol) of 2,5-dibromo-1H-benzimidazole and 0.85 mL (10.18 mmol) of pyrrolidine in 45 mL of acetonitrile is heated for 2 hours at 150° C. in the microwave. The reaction mixture is poured onto water and extracted with EtOAc. The organic phase is washed three times with water and dried over sodium sulfate. The solvent is distilled off, and the residue is stirred with DIPE and the solid is filtered off. Yield: 0.43 g (45% of theoretical); C11H12BrN3 (M=266.13); calc.: molpeak (M−H)—: 264/266; found: molpeak (M−H)−: 264/266; Rf value: 0.5 (silica gel, DCM/MeOH 10:1).

Workup

  1. additionThe reaction mixture is poured onto water
  2. extractionextracted with EtOAc
  3. washThe organic phase is washed three times with water
  4. dry with materialdried over sodium sulfate
  5. distillationThe solvent is distilled off
  6. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-19bdff5b5cd8484c9c60883dc98417d3
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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