Ethyl bromoacetate → HCID 14390438, compound

HRID 1709560Notes

Reaction equation

HRID 1709560 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:18][C:13]3=[N:14][CH:15]=[CH:16][CH:17]=[C:12]3[N:11]=2)=[CH:6][CH:5]=1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>O>[ClH:3].[CH2:24]([O:23][C:21](=[O:22])[CH2:20][N:11]1[C:12]2[C:13](=[N:14][CH:15]=[CH:16][CH:17]=2)[N:18]=[C:10]1[C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1)[CH3:25]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 178477971HCID 178477971, compound

Product 1

HCID 14390438HCID 14390438, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen flow, sodium hydride (1.76 g, 0.044 mole, 60% in oil) was washed with hexanes (~75 ml) and decanted. Dimethylformamide (150 ml) was added and the 2-(4-chlorophenyl)-3H-imidazo[4,5-b]pyridine (9.16 g, 0.04 mole) was added in portions. The reaction mixture was heated at 70°-85° C. for 11/2 hours. Ethyl bromoacetate (6.68 g, 0.04 mole) was added dropwise and the reaction mixture was allowed to stir at room temperature over the weekend. The reaction mixture was poured into water and the precipitate was collected by filtration, washed with water, and dried under high vacuum at 50° C. overnight (78.6% crude yield). A 1.5-g sample was dissolved in ethyl acetate, acidified with ethereal hydrogen chloride, and the crystalline precipitate was collected by filtration, washed with ethyl acetate, and dried under high vacuum to give 1.55 g. The sample was recrystallized from acetonitrile to give 1.6 g after drying under high vacuum at 75° C. over the weekend, mp 199°-200° C. with decomposition.

Workup

  1. customdecanted
  2. additionDimethylformamide (150 ml) was added
  3. temperatureThe reaction mixture was heated at 70°-85° C. for 11/2 hours
  4. filtrationthe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under high vacuum at 50° C. overnight (78.6% crude yield)
  7. dissolutionA 1.5-g sample was dissolved in ethyl acetate
  8. filtrationthe crystalline precipitate was collected by filtration
  9. washwashed with ethyl acetate
  10. customdried under high vacuum
  11. customto give 1.55 g
  12. customThe sample was recrystallized from acetonitrile
  13. customto give 1.6 g
  14. customafter drying under high vacuum at 75° C. over the weekend, mp 199°-200° C. with decomposition

Sources & evidence

ORD record
ord-ec945efcfc184a08b8f24cbcc63e40ce
Source dataset
uspto-grants-1990_08
Patent number
US04948800

Reaction notes

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