Ethyl Bromide → HCID 10894887, compound

HRID 890999Notes

Reaction equation

HRID 890999 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.[CH2:14]([O:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]([Br:29])=[C:25]([Br:30])[C:24]1=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl.O1CCCC1>[CH2:3]([Mg:1][Br:29])[CH3:4].[CH2:14]([O:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]([C:7]2[C:8]3[C:13](=[N:12][CH:11]=[CH:10][CH:9]=3)[NH:5][CH:6]=2)=[C:25]([Br:30])[C:24]1=[O:31])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

10

Reactant 5

HCID 6332Ethyl BromideHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 11122331N-benzyloxymethyl-2,3-dibromomaleimide

Product 2

HCID 10894887HCID 10894887, compoundHCID 178418443HCID 178418443, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethylmagnesium bromide is prepared, starting from magnesium (6.00 mmol) suspended in bromoethane (6.00 mmol) and dry tetrahydrofuran (2.5 ml). The solution is stirred at ambient temperature for 1 hour and then 7-azaindole (6.00 mmol), dissolved in 20 ml of anhydrous toluene, is added dropwise. After stirring at ambient temperature for 1 hour 30 minutes, a solution of N-benzyloxymethyl-2,3-dibromomaleimide (2.01 mmol) in 20 ml of anhydrous toluene is added dropwise. After 20 minutes, 30 ml of dry dichloromethane are added; the reaction mixture is then stirred at 40° C. for 65 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, and then toluene/ethyl acetate: 7/3), 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

Sources & evidence

ORD record
ord-f4d5645fc5e44abeaed25a78734ab150
Source dataset
uspto-grants-2006_02
Patent number
US07001906B2

Reaction notes

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