1,2-Dibromoethane → HCID 66604616, compound

HRID 2410887Notes

Reaction equation

HRID 2410887 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([Cl:37])[CH:31]=2)[CH:7]=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([N:17]3[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]3)[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C([O-])([O-])=O.[K+].[K+].[Br:44][CH2:45][CH2:46]Br.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Br:44][CH2:45][CH2:46][O:36][C:33]1[CH:34]=[CH:35][C:30]([C:6]2[CH:7]=[C:8]3[C:16](=[C:4]([C:1](=[O:3])[NH2:2])[CH:5]=2)[NH:15][C:14]2[CH:13]=[C:12]([N:17]4[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:21][CH2:22]4)[CH:11]=[CH:10][C:9]3=2)=[CH:31][C:32]=1[Cl:37]

Participants

6

Reactant 4

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 66604303HCID 66604303, compound

Product 1

HCID 66604616HCID 66604616, compoundYield 155.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100 ml round bottom flask was loaded with tert-butyl 4-(8-carbamoyl-6-(3-chloro-4-hydroxyphenyl)-9H-carbazol-2-yl)piperazine-1-carboxylate (estimated purity ˜50%, 365 mg, ˜0.35 mmol, Example 409B), K2CO3 (1.12 g, 8.10 mmol), DMF (20 ml) and 1,2-dibromoethane (0.64 ml, 7.4 mmol) and stirred at room temperature for 17 hours. The reaction mixture was poured into a separating funnel that was loaded with 500 ml water+citric acid (0.5 M solution in water) (60 ml, 30 mmol) and extracted with ethyl acetate. The organic layer was washed with dilute (1+5) aq. NaHCO3 solution, then brine, dried over MgSO4, filtered and evaporated to dryness to give 342 mg tert-butyl 4-(6-(4-(2-bromoethoxy)-3-chlorophenyl)-8-carbamoyl-9H-carbazol-2-yl)piperazine-1-carboxylate, which was used without further purification. Estimated purity (from LCMS) ˜55%. MS (ESI) m/e+=627/629/631, m/e−=625/627/629 consistent with isotope pattern for 1 Br and 1 Cl.

Workup

  1. additionThe reaction mixture was poured into a separating funnel that
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed
  4. additionwith dilute (1+5) aq. NaHCO3 solution
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-232739222267440f928cde248617fad1
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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