Ethyl Bromide → HCID 13006214, compound

HRID 891000

Reaction equation

HRID 891000 reaction equation
[Mg:1].Br[CH2:3][CH3:4].[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][N:12]=2)[CH:7]=[CH:6]1.[CH3:14][N:15]1[C:19](=[O:20])[C:18]([Br:21])=[C:17]([Br:22])[C:16]1=[O:23].[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1>[CH2:3]([Mg:1][Br:21])[CH3:4].[Br:22][C:17]1[C:16](=[O:23])[N:15]([CH3:14])[C:19](=[O:20])[C:18]=1[C:7]1[C:8]2[C:13](=[N:12][CH:11]=[CH:10][CH:9]=2)[NH:5][CH:6]=1

Participants

10

Reactant 5

HCID 6332Ethyl BromideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 181552,3-Dibromo-N-methylmaleimideHCID 25517Ammonium ChlorideHCID 5462224Magnesium

Product 2

HCID 13006214HCID 13006214, compoundHCID 178418443HCID 178418443, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethylmagnesium bromide is prepared, starting from magnesium (12.7 mmol) suspended in bromoethane (12.7 mmol) and dry tetrahydrofuran (5 ml). The solution is stirred at ambient temperature for 1 hour and then 7-azaindole (12.7 mmol), dissolved in 40 ml of anhydrous toluene, is added dropwise. After stirring at ambient temperature for 1 hour 30 minutes, a solution of N-methyl-2,3-dibromomaleimide (3.53 mmol) in 40 ml of anhydrous toluene is added dropwise. After 20 minutes, 60 ml of dry dichloromethane are added; the reaction mixture is then stirred at 40° C. for 75 hours and hydrolysed with saturated aqueous ammonium chloride solution. The organic product is extracted with ethyl acetate, and the organic phases are then combined, dried over magnesium sulphate and filtered. After evaporating off the solvent and purifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2), the expected product is isolated.

Workup

  1. additionis added dropwise
  2. stirringAfter stirring at ambient temperature for 1 hour 30 minutes
  3. waitAfter 20 minutes
  4. extractionThe organic product is extracted with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customAfter evaporating off the solvent
  8. custompurifying the residue by chromatography on silica gel (cyclohexane/ethyl acetate: 3/2)

Sources & evidence

ORD record
ord-f2c7b550815040e98b849e8a6a3f822c
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Linked notes

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