1,2-Dibromoethane → HCID 57833259, compound

HRID 729956Notes

Reaction equation

HRID 729956 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH:5]=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=3)=[CH:18][CH:17]=2)[N:3]=1.[Br:30][CH2:31][CH2:32]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Br:30][CH2:31][CH2:32][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]4[CH:28]=[CH:27][N:26]=[C:25]([CH3:29])[CH:24]=4)=[CH:20][CH:21]=3)[CH:5]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 136183340HCID 136183340, compound

Product 1

HCID 57833259HCID 57833259, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Step 2 product (1 equiv) in DMF is added 1,2-dibromoethane (1 equiv) and K2CO3 (3 equiv). The mixture is refluxed overnight. After cooling to rt, the mixture is diluted with EtOAc and washed sequentially with 1N NaOH, water and brine. The organic layer is dried (Na2SO4) and concentrated to afford a crude product which is to be used in next step without further purification.

Workup

  1. temperatureThe mixture is refluxed overnight
  2. washwashed sequentially with 1N NaOH, water and brine
  3. dry with materialThe organic layer is dried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-322ba257e0f2457a81acdb26d7e9414c
Source dataset
uspto-grants-2009_09
Patent number
US07582646B2

Reaction notes

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