1,2-Dibromoethane → HCID 67285070, compound

HRID 2093774Notes

Reaction equation

HRID 2093774 reaction equation
[OH:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:11]=[C:10]([NH:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][CH:3]=1.[Br:36][CH2:37][CH2:38]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:36][CH2:37][CH2:38][O:1][C:2]1[CH:35]=[CH:34][C:5]([CH2:6][NH:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][C:16]([F:19])([F:17])[F:18])[N:11]=[C:10]([NH:20][C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])=[CH:23][CH:22]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-Dibromoethane2×HCID 11430Potassium Carbonate2×HCID 58223050Tert-butyl 4-((4-((4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate

Product 1

HCID 67285070HCID 67285070, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of tert-butyl 4-((4-((4-hydroxybenzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate (4 g, 8.14 mmol), 1,2-dibromoethane (2.1 mL, 24.42 mmol) in acetone (20 mL) was added potassium carbonate (4.50 g, 32.6 mmol). The resulting solution was stirred for 16 h at reflux. Add another 4 eq of potassium carbonate and 3 eq of 1,2-dibromoethane. The mixture was refluxed for another 7 hs. After cooling to rt, the white solid was filtered and washed with actone. The filtrate was concentrated and purified by Biotage eluting with 20-33% ethyl acetate in hexane to give tert-butyl 4-((4-((4-(2-bromoethoxy)benzyl)amino)-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl)amino)benzoate (2.91 g, 60%) as white solid.

Workup

  1. temperatureat reflux
  2. temperatureThe mixture was refluxed for another 7 hs
  3. filtrationthe white solid was filtered
  4. washwashed with actone
  5. concentrationThe filtrate was concentrated
  6. custompurified by Biotage
  7. washeluting with 20-33% ethyl acetate in hexane

Sources & evidence

ORD record
ord-c67eb8e7b43d428288df79a421954fde
Source dataset
uspto-grants-2013_05
Patent number
US08445490B2

Reaction notes

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