1-Bromo-2-Chloroethane → HCID 22715706, compound

HRID 2112393Notes

Reaction equation

HRID 2112393 reaction equation
[N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[NH:3][CH:2]=1.[H-].[Na+].Br[CH2:13][CH2:14][Cl:15].CCCCCCC>CN(C=O)C>[Cl:15][CH2:14][CH2:13][N:3]1[C:4]2=[N:5][CH:6]=[CH:7][CH:8]=[C:9]2[N:1]=[CH:2]1

Participants

6

Reactant 4

HCID 78491-Bromo-2-ChloroethaneHCID 8900HeptaneHCID 24758Sodium hydrideHCID 178420746HCID 178420746, compound

Product 1

HCID 22715706HCID 22715706, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

6.5 g (54.56 mmol) 3H-imidazo[4,5-b]pyridine were dissolved under argon in 100 ml DMF and cooled to 0° C. in an ice bath. 4.6 g (109.1 mmol) sodium hydride were added and the mixture was stirred for 1 hour at room temperature. Then a solution of 9 ml (109.1 mmol) 1-bromo-2-chloroethane in 30 ml DMF was added over the period of an hour and the solution was stirred at room temperature during 20 hours. The brownish solution was poured onto ice water and extracted 3 times with ethyl acetate. The organic layers were combined, washed once with brine, dried over Na2SO4 and evaporated in vacuo to give a yellow oil. The oil was stirred with three times 50 ml warm heptane. Heptane was decanted, the tree fractions pooled and evaporated to give 2.08 g of light yellow crystals. MS(ISP): 182.2 [MH]+; 1H-NMR (CDCl3): 3.99 (t, 2H), 4.66 (t, 2H), 7.28-7.32 (m, 1H), 8.11-8.17 (m, 2H), 8.40-8.42 (m, 1H).

Workup

  1. stirringthe solution was stirred at room temperature during 20 hours
  2. additionThe brownish solution was poured onto ice water
  3. extractionextracted 3 times with ethyl acetate
  4. washwashed once with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customto give a yellow oil
  8. stirringThe oil was stirred with three times 50 ml
  9. customHeptane was decanted
  10. customevaporated

Sources & evidence

ORD record
ord-43a3217a2fe64228bc0bd8e960681c29
Source dataset
uspto-grants-2009_04
Patent number
US07524823B2

Reaction notes

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